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

HRID 1268505Notes

Reaction equation

HRID 1268505 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-8199ce378393461980c4a86fbaac6988
Source dataset
uspto-grants-2003_04
Patent number
US06555699B2

Reaction notes

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