Tetrahydrofuran → 1alpha,3beta-bis(tert-Butyldimethylsilyloxy)-20(S) {(Z)-4-methyl-4-triethylsilyloxy-2-pentenylthio}pregna-5,7,16-triene

HRID 2268299Notes

Reaction equation

HRID 2268299 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@:37]2([CH3:38])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([S:23][C:24](OC2C=CC=CC=2)=O)[CH3:22])[CH2:12][C@@H:11]([O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].BrC/[CH:50]=[CH:51]\[C:52]([CH3:62])([O:54][Si:55]([CH2:60][CH3:61])([CH2:58][CH3:59])[CH2:56][CH3:57])[CH3:53].O1CCCC1.[OH-].[K+]>CO>[Si:1]([O:8][C@@H:9]1[C@@:37]2([CH3:38])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([S:23][CH2:24]/[CH:50]=[CH:51]\[C:52]([CH3:53])([O:54][Si:55]([CH2:60][CH3:61])([CH2:56][CH3:57])[CH2:58][CH3:59])[CH3:62])[CH3:22])[CH2:12][C@@H:11]([O:40][Si:41]([C:44]([CH3:46])([CH3:45])[CH3:47])([CH3:43])[CH3:42])[CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 120195111alpha,3beta-bis(tert-butyldimethylsilyloxy)-20(S)-phenoxycarbonylthiopregna-5,7,16-trieneHCID 86584697(Z)-1-bromo-4-methyl-4-triethylsilyloxy-2-pentene

Product 1

HCID 700090241alpha,3beta-bis(tert-Butyldimethylsilyloxy)-20(S) {(Z)-4-methyl-4-triethylsilyloxy-2-pentenylthio}pregna-5,7,16-trieneYield 64.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under the same conditions as in Example 3, 1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-phenoxycarbonylthiopregna-5,7,16-triene (91.2 mg, 0.131 mmol), (Z)-1-bromo-4-methyl-4-triethylsilyloxy-2-pentene (192 mg, 0.655 mmol), tetrahydrofuran (1.5 ml) and 1M KOH solution in methanol (1.5 ml) were reacted and worked up, and then the residue was purified by preparative thin layer chromatography (0.5 mm×2, hexane:dichloromethane:ethyl acetate=160:40:1, developed once) to give the title compound as a colorless oil (66.3 mg, 64%).

Workup

  1. customthe residue was purified by preparative thin layer chromatography (0.5 mm×2, hexane

Sources & evidence

ORD record
ord-7293b25623014b0b8280db537b76a14f
Source dataset
uspto-grants-2001_12
Patent number
US06326503B1

Reaction notes

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