Реакция #1477969

ord-c7168d164d3c4698b9958b6a86c79cd4

Уравнение реакции

CC(=O)O.CC(C)(C)[Si](C)(C)OC1CC[C@@]2(CO)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
3-t-butyldimethylsiloxy-19-hydroxy-5-androsten-17-one acetate
CC(=O)[O-]
acetate
→
CC(C)(C)[Si](C)(C)OC1CC[C@@]2(CO)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]32)C1
3-t-butyldimethylsiloxy-5-androsten-17β,19-diol

Реактанты

—
19-hydroxy-3β-(2'-tetrahydropyranyloxy)-5-androsten-17-one
CC(=O)O.CC(C)(C)[Si](C)(C)OC1CC[C@@]2(CO)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
3-t-butyldimethylsiloxy-19-hydroxy-5-androsten-17-one acetate
CC(=O)[O-]
acetate
—
19-hydroxy-3β-(4'-tetrahydropyranyloxy)-5-androsten-17-one acetate

Реагенты

Нет

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Методика

Substituting 3-t-butyldimethylsiloxy-19-hydroxy-5-androsten-17-one acetate and 19-hydroxy-3β-(4'-tetrahydropyranyloxy)-5-androsten-17-one acetate for the 19-hydroxy-3β-(2'-tetrahydropyranyloxy)-5-androsten-17-one, acetate above results in the preparation of 3-t-butyldimethylsiloxy-5-androsten-17β,19-diol and 3β-(4'-tetrahydropyranyloxy)-5-androstene-17β,19-diol, respectively.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US04139617uspto-grants-1979_02