20-(5,5-Dimethyl-1,3-dioxan-2-yl)-3beta-(tert-butyldimethylsilyl)oxypregn-6-ene-1alpha,5alpha-diol → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)-3beta-(tertbutyldimethylsilyl)oxy-1alpha-(methoxymethyl)oxypregn-6-en-5alpha-ol

HRID 1196363Notes

Reaction equation

HRID 1196363 reaction equation
[CH3:1][C:2]1([CH3:39])[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]([OH:38])([CH2:18][C@@H:19]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:20][C@@H:21]3[OH:29])[CH:16]=[CH:15]4)[CH2:12][CH2:11]2)[CH3:9])[O:4][CH2:3]1.[O:40]1[CH2:44]CO[CH:41]1C([C@@H]1[C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)[C@](O)(C[C@@H](O)C[C@@H]2O)C=C3)CC1)C>>[CH3:39][C:2]1([CH3:1])[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]([OH:38])([CH2:18][C@@H:19]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:20][C@@H:21]3[O:29][CH2:41][O:40][CH3:44])[CH:16]=[CH:15]4)[CH2:12][CH2:11]2)[CH3:9])[O:4][CH2:3]1

Participants

3

Reactant 2

HCID 6785292820-(5,5-Dimethyl-1,3-dioxan-2-yl)-3beta-(tert-butyldimethylsilyl)oxypregn-6-ene-1alpha,5alpha-diolHCID 6785299520-(1,3-Dioxolan-2-yl)pregn-6-ene-1alpha,3beta,5alpha-triol

Product 1

HCID 6785294620-(5,5-Dimethyl-1,3-dioxan-2-yl)-3beta-(tertbutyldimethylsilyl)oxy-1alpha-(methoxymethyl)oxypregn-6-en-5alpha-olYield 74.2%

Procedure

The reaction and workup procedures of Example 110 were repeated except that 400 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-3β-(tert-butyldimethylsilyl)oxypregn-6-ene-1α,5α-diol was used in lieu of 400 mg of 20-(1,3-dioxolan-2-yl)pregn-6-ene-1α,3β,5α-triol to give 320 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-3β-(tertbutyldimethylsilyl)oxy-1α-(methoxymethyl)oxypregn-6-en-5α-ol showing the following physical properties.

Workup

  1. customThe reaction and workup procedures of Example 110

Sources & evidence

ORD record
ord-0830ad0b52bf46c2ac6824ece4b7b200
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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