20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,3beta,7alpha-tris(methoxycarbonyloxy)pregn-5-ene → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)-3beta-(tert-butyldimethylsilyl)oxy-1alpha-(methoxymethyl)oxypregn-5-en-7alpha-ol

HRID 1708810Notes

Reaction equation

HRID 1708810 reaction equation
[CH3:1][C:2]1([CH3:46])[CH2:7][O:6][CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C@H:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17]([CH2:18][C@@H:19]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH2:20][C@@H:21]3[O:29][CH2:30][O:31][CH3:32])=[CH:16][C@H:15]4[O:41]C(OC)=O)[CH2:12][CH2:11]2)[CH3:9])[O:4][CH2:3]1.CC1(C)COC(C([C@@H]2[C@]3(C)[C@H]([C@H]4[C@H](CC3)[C@]3(C)C(C[C@@H](OC(OC)=O)C[C@@H]3OC(OC)=O)=C[C@H]4OC(OC)=O)CC2)C)OC1>>[CH3:46][C:2]1([CH3:1])[CH2:3][O:4][CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C@H:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17]([CH2:18][C@@H:19]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:35])[CH3:36])[CH2:20][C@@H:21]3[O:29][CH2:30][O:31][CH3:32])=[CH:16][C@H:15]4[OH:41])[CH2:12][CH2:11]2)[CH3:9])[O:6][CH2:7]1

Participants

3

Reactant 2

HCID 5714185820-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,3beta,7alpha-tris(methoxycarbonyloxy)pregn-5-eneHCID 6785295620-(5,5-Dimethyl-1,3-dioxan-2-yl)-3beta-(tert-butyldimethylsilyl)oxy-1alpha-(methoxymethyl)oxy-7alpha-(methoxycarbonyl)oxypregn-5-ene

Product 1

HCID 1865587320-(5,5-Dimethyl-1,3-dioxan-2-yl)-3beta-(tert-butyldimethylsilyl)oxy-1alpha-(methoxymethyl)oxypregn-5-en-7alpha-olYield 59.3%

Procedure

The reaction and workup procedures of Example 140 were repeated except that 120 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-3β-(tert-butyldimethylsilyl)oxy-1α-(methoxymethyl)oxy-7α-(methoxycarbonyl)oxypregn-5 -ene was used in lieu of 100 mg of 20-(5,5-dimethyl-1,3 -dioxan-2-yl)-1α,3β,7α-tris (methoxycarbonyloxy)pregn-5-ene to give 65 mg of 20-(5,5-dimethyl-1,3-dioxan-2yl)-3β-(tert-butyldimethylsilyl)oxy-1α-(methoxymethyl)oxypregna-5-en-7α-ol showing the following physical properties.

Workup

  1. customThe reaction and workup procedures of Example 140

Sources & evidence

ORD record
ord-b2e4ed6336d14ebd83ec4b39e7ab4530
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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