(1R,2R,3S,4S)-2-[(2R,3S)-2,3-Di­methyl­oxiran-2-yl]-3,4-bis(4-methoxy­benzyl­oxy)­cyclo­hexanol

Kani, Y.; Ohba, S.; Amano, S.; Ogawa, N.; Ohtsuka, M.; Chida, N.

doi:10.1107/S0108270100005606

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(1R,2R,3S,4S)-2-[(2R,3S)-2,3-Dimethyloxiran-2-yl]-3,4-bis(4-methoxybenzyloxy)cyclohexanol

Y. Kani, S. Ohba, S. Amano, N. Ogawa, M. Ohtsuka and N. Chida

The relative configuration was determined for the title compound, C₂₆H₃₄O₆, which was prepared in a synthetic study on immunosuppressant FR65814. There is an intramolecular hydrogen bond between the hydroxy and epoxy groups.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100005606/qa0281sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270100005606/qa0281Isup2.hkl Contains datablock I

CCDC reference: 145659

Comment top

The total synthesis of novel immunosuppressant FR65814 was reported (Amano et al., 1998, 1999). The title compound, (I), was prepared in a synthetic study on FR65814.

Experimental top

The title compound was synthesized from D-glucose (Amano et al., 1999). The stereochemistries at C-3 and C-4 (atom labels C3 and C4, respectively) came from those at C-2 and C-3 of D-glucose, respectively.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

(I) top

Crystal data top

C₂₆H₃₄O₆	D_x = 1.209 Mg m⁻³
M_r = 442.55	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 25 reflections
Hall symbol: P 2ac 2ab	θ = 10–15°
a = 18.060 (3) Å	µ = 0.09 mm⁻¹
b = 23.477 (3) Å	T = 296 K
c = 5.736 (2) Å	Prism, colourless
V = 2431 (1) Å³	0.6 × 0.4 × 0.4 mm
Z = 4

Data collection top

Rigaku AFC-5S diffractometer	θ_max = 25°
θ–2θ scans	h = 0→21
2493 measured reflections	k = 0→28
2493 independent reflections	l = 0→7
1281 reflections with I > 2σ(I)	3 standard reflections every 100 reflections
R_int = 0	intensity decay: none

Refinement top

Refinement on F²	H-atom parameters not refined
R[F² > 2σ(F²)] = 0.073	w = 1/[σ²(F_o²) + {0.05(F_o² + 2F_c²)/3}²]
wR(F²) = 0.221	(Δ/σ)_max = 0.010
S = 1.92	Δρ_max = 0.21 e Å⁻³
2493 reflections	Δρ_min = −0.19 e Å⁻³
292 parameters	Absolute structure: see text, no Friedel pairs

Crystal data top

C₂₆H₃₄O₆	V = 2431 (1) Å³
M_r = 442.55	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 18.060 (3) Å	µ = 0.09 mm⁻¹
b = 23.477 (3) Å	T = 296 K
c = 5.736 (2) Å	0.6 × 0.4 × 0.4 mm

Data collection top

Rigaku AFC-5S diffractometer	R_int = 0
2493 measured reflections	3 standard reflections every 100 reflections
2493 independent reflections	intensity decay: none
1281 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.073	H-atom parameters not refined
wR(F²) = 0.221	Δρ_max = 0.21 e Å⁻³
S = 1.92	Δρ_min = −0.19 e Å⁻³
2493 reflections	Absolute structure: see text, no Friedel pairs
292 parameters

Special details top

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.9626 (3)	−0.3139 (2)	−1.1771 (7)	0.094 (2)
O2	−0.8426 (3)	−0.2499 (2)	−1.2545 (7)	0.096 (1)
O3	−0.9397 (2)	−0.1625 (1)	−0.7384 (6)	0.065 (1)
O4	−0.8297 (2)	0.0731 (2)	−0.3631 (10)	0.110 (2)
O5	−1.0898 (2)	−0.1989 (2)	−0.6585 (7)	0.078 (1)
O6	−1.3556 (3)	−0.0363 (2)	−0.355 (1)	0.151 (3)
C1	−0.9335 (4)	−0.3146 (3)	−0.945 (1)	0.078 (2)
C2	−0.9067 (3)	−0.2553 (2)	−0.8673 (9)	0.060 (1)
C3	−0.9710 (3)	−0.2142 (2)	−0.8387 (10)	0.060 (1)
C4	−1.0301 (3)	−0.2383 (2)	−0.6780 (10)	0.068 (2)
C5	−1.0576 (3)	−0.2938 (3)	−0.766 (1)	0.087 (2)
C6	−0.9948 (4)	−0.3375 (3)	−0.787 (1)	0.091 (2)
C7	−0.8425 (3)	−0.2344 (3)	−1.010 (1)	0.071 (2)
C8	−0.8526 (3)	−0.1918 (3)	−1.200 (1)	0.083 (2)
C9	−0.7952 (4)	−0.1503 (4)	−1.278 (1)	0.122 (3)
C10	−0.7688 (3)	−0.2426 (4)	−0.898 (1)	0.118 (3)
C11	−0.9723 (3)	−0.1107 (2)	−0.821 (1)	0.081 (2)
C12	−0.9355 (3)	−0.0630 (2)	−0.696 (1)	0.076 (2)
C13	−0.8669 (4)	−0.0438 (3)	−0.756 (1)	0.093 (2)
C14	−0.8318 (4)	0.0014 (3)	−0.640 (2)	0.105 (3)
C15	−0.8666 (4)	0.0281 (3)	−0.462 (1)	0.088 (2)
C16	−0.9358 (4)	0.0098 (3)	−0.393 (1)	0.107 (3)
C17	−0.9685 (4)	−0.0362 (3)	−0.508 (1)	0.105 (3)
C18	−0.8662 (5)	0.1021 (3)	−0.173 (2)	0.126 (3)
C19	−1.1092 (4)	−0.1854 (3)	−0.433 (1)	0.098 (2)
C20	−1.1727 (4)	−0.1431 (3)	−0.424 (1)	0.081 (2)
C21	−1.2256 (3)	−0.1431 (3)	−0.593 (1)	0.093 (2)
C22	−1.2874 (4)	−0.1058 (3)	−0.576 (1)	0.091 (2)
C23	−1.2947 (4)	−0.0730 (3)	−0.389 (1)	0.093 (2)
C24	−1.2427 (4)	−0.0730 (3)	−0.226 (1)	0.104 (3)
C25	−1.1814 (4)	−0.1068 (3)	−0.239 (1)	0.101 (3)
C26	−1.4026 (5)	−0.0300 (6)	−0.527 (3)	0.215 (6)
H1	−0.924	−0.289	−1.23	0.1263*
H2	−0.8923	−0.3405	−0.9403	0.0938*
H3	−0.8872	−0.2607	−0.7132	0.0724*
H4	−0.9923	−0.2058	−0.9883	0.0725*
H5	−1.0088	−0.2440	−0.5263	0.0819*
H6	−1.0944	−0.3082	−0.6606	0.1048*
H7	−1.0795	−0.2882	−0.9172	0.1048*
H8	−1.0140	−0.3722	−0.8523	0.1093*
H9	−0.9748	−0.3450	−0.6353	0.1093*
H10	−0.9026	−0.1786	−1.2177	0.0994*
H11	−0.7484	−0.1603	−1.2100	0.1461*
H12	−0.7914	−0.1513	−1.4444	0.1461*
H13	−0.8090	−0.1127	−1.2282	0.1461*
H14	−0.7548	−0.2819	−0.9086	0.1411*
H15	−0.7326	−0.2196	−0.9765	0.1411*
H16	−0.7716	−0.2315	−0.7373	0.1411*
H17	−0.9646	−0.1070	−0.9858	0.0977*
H18	−1.0244	−0.1105	−0.7883	0.0977*
H19	−0.8415	−0.0620	−0.8830	0.1116*
H20	−0.7831	0.0133	−0.6861	0.1254*
H21	−0.9612	0.0284	−0.2675	0.1280*
H22	−1.0157	−0.0498	−0.4547	0.1258*
H23	−0.8353	0.1326	−0.1182	0.1515*
H24	−0.9125	0.1174	−0.2263	0.1515*
H25	−0.8750	0.0758	−0.0481	0.1515*
H26	−1.1238	−0.2196	−0.3539	0.1176*
H27	−1.0670	−0.1691	−0.3563	0.1176*
H28	−1.2211	−0.1682	−0.7244	0.1115*
H29	−1.3235	−0.1043	−0.6987	0.1087*
H30	−1.2484	−0.0482	−0.0940	0.1250*
H31	−1.1446	−0.1052	−0.1182	0.1215*
H32	−1.4410	−0.0041	−0.4810	0.2581*
H33	−1.3772	−0.0151	−0.6608	0.2581*
H34	−1.4240	−0.0663	−0.5655	0.2581*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.123 (4)	0.094 (3)	0.064 (3)	−0.006 (3)	−0.037 (3)	−0.009 (3)
O2	0.118 (3)	0.106 (3)	0.063 (2)	0.007 (3)	0.010 (3)	−0.013 (3)
O3	0.067 (2)	0.065 (2)	0.065 (2)	0.010 (2)	−0.011 (2)	−0.012 (2)
O4	0.099 (3)	0.092 (3)	0.140 (5)	−0.013 (3)	−0.012 (3)	−0.034 (3)
O5	0.064 (2)	0.105 (3)	0.066 (2)	0.016 (2)	−0.002 (2)	0.004 (2)
O6	0.103 (4)	0.146 (5)	0.203 (7)	0.037 (3)	0.015 (4)	0.039 (5)
C1	0.100 (4)	0.071 (3)	0.063 (3)	0.011 (3)	−0.024 (3)	−0.016 (3)
C2	0.077 (3)	0.061 (3)	0.044 (3)	0.016 (2)	−0.012 (3)	−0.001 (3)
C3	0.059 (3)	0.066 (3)	0.056 (3)	0.001 (2)	−0.013 (2)	0.003 (3)
C4	0.068 (3)	0.079 (3)	0.058 (3)	0.002 (2)	−0.005 (3)	0.014 (3)
C5	0.094 (4)	0.082 (3)	0.086 (4)	−0.024 (3)	−0.009 (5)	0.012 (4)
C6	0.115 (4)	0.077 (4)	0.081 (5)	−0.008 (3)	−0.018 (4)	0.017 (4)
C7	0.066 (3)	0.083 (4)	0.063 (2)	0.021 (3)	−0.006 (2)	−0.006 (2)
C8	0.086 (4)	0.105 (3)	0.058 (4)	0.024 (3)	0.005 (4)	0.002 (3)
C9	0.105 (5)	0.160 (7)	0.100 (6)	−0.022 (4)	0.045 (5)	0.022 (6)
C10	0.068 (4)	0.180 (7)	0.104 (6)	0.021 (5)	−0.018 (4)	0.031 (6)
C11	0.093 (4)	0.064 (3)	0.088 (5)	0.011 (3)	−0.027 (4)	0.001 (3)
C12	0.076 (3)	0.053 (3)	0.099 (5)	0.015 (3)	−0.013 (3)	0.003 (3)
C13	0.081 (4)	0.097 (5)	0.101 (5)	0.006 (3)	0.019 (4)	−0.027 (4)
C14	0.077 (4)	0.106 (5)	0.131 (7)	−0.009 (4)	0.018 (4)	−0.033 (4)
C15	0.089 (4)	0.068 (4)	0.108 (5)	0.012 (3)	−0.013 (3)	−0.002 (3)
C16	0.102 (4)	0.114 (5)	0.104 (6)	−0.014 (4)	0.031 (5)	−0.051 (5)
C17	0.087 (5)	0.112 (5)	0.115 (6)	−0.014 (4)	0.021 (4)	−0.041 (4)
C18	0.147 (7)	0.108 (6)	0.123 (7)	0.009 (5)	−0.026 (5)	−0.047 (5)
C19	0.093 (5)	0.130 (6)	0.072 (3)	0.037 (4)	0.016 (4)	0.010 (4)
C20	0.071 (4)	0.107 (5)	0.066 (4)	−0.001 (3)	0.012 (3)	0.017 (3)
C21	0.084 (4)	0.119 (5)	0.076 (4)	0.013 (3)	−0.008 (3)	−0.009 (5)
C22	0.081 (4)	0.111 (6)	0.080 (5)	0.009 (3)	−0.027 (4)	0.004 (4)
C23	0.092 (4)	0.100 (5)	0.088 (5)	−0.012 (3)	0.011 (4)	0.003 (4)
C24	0.105 (5)	0.118 (6)	0.090 (5)	0.009 (4)	0.001 (4)	−0.031 (5)
C25	0.093 (5)	0.134 (6)	0.077 (5)	0.006 (4)	−0.010 (5)	−0.020 (4)
C26	0.137 (8)	0.27 (1)	0.24 (1)	0.092 (9)	−0.043 (8)	0.01 (1)

Geometric parameters (Å, º) top

O1—C1	1.429 (10)	C10—H15	0.960
O1—H1	0.960	C10—H16	0.960
O2—C7	1.45 (1)	C11—C12	1.48 (1)
O2—C8	1.411 (10)	C11—H17	0.960
O3—C3	1.457 (8)	C11—H18	0.960
O3—C11	1.431 (8)	C12—C13	1.36 (1)
O4—C15	1.37 (1)	C12—C17	1.38 (1)
O4—C18	1.45 (1)	C13—C14	1.41 (1)
O5—C4	1.424 (8)	C13—H19	0.960
O5—C19	1.38 (1)	C14—C15	1.35 (1)
O6—C23	1.41 (1)	C14—H20	0.960
O6—C26	1.31 (2)	C15—C16	1.38 (1)
C1—C2	1.54 (1)	C16—C17	1.40 (1)
C1—C6	1.53 (1)	C16—H21	0.960
C1—H2	0.960	C17—H22	0.960
C2—C3	1.521 (10)	C18—H23	0.960
C2—C7	1.50 (1)	C18—H24	0.960
C2—H3	0.960	C18—H25	0.960
C3—C4	1.519 (10)	C19—C20	1.52 (1)
C3—H4	0.960	C19—H26	0.960
C4—C5	1.48 (1)	C19—H27	0.960
C4—H5	0.960	C20—C21	1.36 (1)
C5—C6	1.53 (1)	C20—C25	1.37 (1)
C5—H6	0.960	C21—C22	1.42 (1)
C5—H7	0.960	C21—H28	0.960
C6—H8	0.960	C22—C23	1.33 (1)
C6—H9	0.960	C22—H29	0.960
C7—C8	1.49 (1)	C23—C24	1.33 (1)
C7—C10	1.49 (1)	C24—C25	1.36 (1)
C8—C9	1.49 (1)	C24—H30	0.960
C8—H10	0.960	C25—H31	0.960
C9—H11	0.960	C26—H32	0.960
C9—H12	0.960	C26—H33	0.960
C9—H13	0.960	C26—H34	0.960
C10—H14	0.960

O1···C4ⁱ	3.590 (9)	O3···C8ⁱⁱⁱ	3.534 (10)
O1···C6ⁱ	3.59 (1)	C4···H1ⁱⁱⁱ	3.4 (1)
O2···C21ⁱⁱ	3.40 (1)

C1—O1—H1	90	H14—C10—H15	109.5
C7—O2—C8	62.7 (5)	H14—C10—H16	109
C3—O3—C11	114.7 (5)	H15—C10—H16	109
C15—O4—C18	117.0 (8)	O3—C11—C12	107.3 (6)
C4—O5—C19	114.6 (6)	O3—C11—H17	110.0
C23—O6—C26	118 (1)	O3—C11—H18	110.0
O1—C1—C2	112.0 (7)	C12—C11—H17	110.0
O1—C1—C6	106.8 (7)	C12—C11—H18	110.0
O1—C1—H2	108.7	H17—C11—H18	109.5
C2—C1—C6	111.9 (7)	C11—C12—C13	122.4 (9)
C2—C1—H2	108.7	C11—C12—C17	121.7 (9)
C6—C1—H2	108.7	C13—C12—C17	115.9 (9)
C1—C2—C3	111.5 (6)	C12—C13—C14	122.8 (9)
C1—C2—C7	112.3 (7)	C12—C13—H19	118.6
C1—C2—H3	105.3	C14—C13—H19	118.6
C3—C2—C7	116.1 (6)	C13—C14—C15	119.9 (9)
C3—C2—H3	105.3	C13—C14—H20	120
C7—C2—H3	105.3	C15—C14—H20	120
O3—C3—C2	106.0 (5)	O4—C15—C14	116.3 (9)
O3—C3—C4	110.1 (6)	O4—C15—C16	124.1 (10)
O3—C3—H4	109.8	C14—C15—C16	119.6 (10)
C2—C3—C4	111.4 (6)	C15—C16—C17	119.2 (9)
C2—C3—H4	109.8	C15—C16—H21	120.4
C4—C3—H4	109.8	C17—C16—H21	120.4
O5—C4—C3	109.7 (6)	C12—C17—C16	122.6 (9)
O5—C4—C5	110.1 (6)	C12—C17—H22	118.7
O5—C4—H5	108.7	C16—C17—H22	118.7
C3—C4—C5	110.8 (7)	O4—C18—H23	109
C3—C4—H5	108.7	O4—C18—H24	109
C5—C4—H5	108.7	O4—C18—H25	109.5
C4—C5—C6	111.5 (7)	H23—C18—H24	109.5
C4—C5—H6	109.0	H23—C18—H25	109
C4—C5—H7	109.0	H24—C18—H25	109
C6—C5—H6	109.0	O5—C19—C20	112.1 (8)
C6—C5—H7	109.0	O5—C19—H26	108.8
H6—C5—H7	109.5	O5—C19—H27	108.8
C1—C6—C5	110.3 (7)	C20—C19—H26	108.8
C1—C6—H8	109.3	C20—C19—H27	108.8
C1—C6—H9	109.3	H26—C19—H27	109.5
C5—C6—H8	109.3	C19—C20—C21	120.3 (9)
C5—C6—H9	109.3	C19—C20—C25	121.4 (9)
H8—C6—H9	109.5	C21—C20—C25	118.2 (9)
O2—C7—C2	116.4 (7)	C20—C21—C22	120.1 (9)
O2—C7—C8	57.5 (5)	C20—C21—H28	120.0
O2—C7—C10	112.7 (8)	C22—C21—H28	120.0
C2—C7—C8	121.7 (7)	C21—C22—C23	119.4 (9)
C2—C7—C10	114.2 (7)	C21—C22—H29	120
C8—C7—C10	120.8 (9)	C23—C22—H29	120
O2—C8—C7	59.8 (5)	O6—C23—C22	122 (1)
O2—C8—C9	118.5 (7)	O6—C23—C24	117 (1)
O2—C8—H10	114.2	C22—C23—C24	120 (1)
C7—C8—C9	124.9 (8)	C23—C24—C25	122 (1)
C7—C8—H10	114.2	C23—C24—H30	118
C9—C8—H10	114.2	C25—C24—H30	118
C8—C9—H11	109.5	C20—C25—C24	119.7 (10)
C8—C9—H12	109.5	C20—C25—H31	120
C8—C9—H13	109.5	C24—C25—H31	120
H11—C9—H12	109.5	O6—C26—H32	109
H11—C9—H13	109	O6—C26—H33	109
H12—C9—H13	109	O6—C26—H34	109
C7—C10—H14	109.5	H32—C26—H33	109
C7—C10—H15	109.5	H32—C26—H34	109
C7—C10—H16	109.5	H33—C26—H34	109

Symmetry codes: (i) x, y, z−1; (ii) x+1/2, −y−1/2, −z−2; (iii) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.96	1.73	2.673 (9)	166

Experimental details

Crystal data
Chemical formula	C₂₆H₃₄O₆
M_r	442.55
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	18.060 (3), 23.477 (3), 5.736 (2)
V (Å³)	2431 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.6 × 0.4 × 0.4

Data collection
Diffractometer	Rigaku AFC-5S diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2493, 2493, 1281
R_int	0
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.221, 1.92
No. of reflections	2493
No. of parameters	292
No. of restraints	?
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19
Absolute structure	See text, no Friedel pairs

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SIR92 (Altomare et al., 1994), TEXSAN.

Selected geometric parameters (Å, º) top

O1—C1	1.429 (10)	O3—C3	1.457 (8)
O2—C7	1.45 (1)	O5—C4	1.424 (8)
O2—C8	1.411 (10)	C7—C8	1.49 (1)

C7—O2—C8	62.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.96	1.73	2.673 (9)	166

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(1R,2R,3S,4S)-2-[(2R,3S)-2,3-Di­methyl­oxiran-2-yl]-3,4-bis(4-methoxy­benzyl­oxy)­cyclo­hexanol

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(1R,2R,3S,4S)-2-[(2R,3S)-2,3-Dimethyloxiran-2-yl]-3,4-bis(4-methoxybenzyloxy)cyclohexanol