A steroid structure which refutes the isolation of C(17)-C(20) rotational isomers

Charles M. Weeks; Gert J. Kruger; William L. Duax; Makino Takuo; Osawa Yoshio

doi:10.1016/0039-128X(77)90044-7

A steroid structure which refutes the isolation of C(17)-C(20) rotational isomers

Charles M. Weeks
, Gert J. Kruger
, William L. Duax
, Makino Takuo
, Osawa Yoshio

Department of Structural Biology

Hauptman-Woodward Medical Research Institute, Inc.

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

Isolation of two C(17)-C(20) rotamers of 20-methyl-20-(2-hydroxy-ethoxy)-5-pregnene-3β, 17α-diol has been reported. X-Ray analysis of a diacetate derivative of one of the "rotamers" shows that the actual structure is 3β-acetoxy-17aα-(2-acetoxyethoxy)-17α,17aβ-dimethyl-D-homo-5-androsten-17β-ol (C₂₈H₄₄O₆). Thus, although this investigation refutes the existence of C(17)-C(20) rotamers, it suggests a possible new pathway for D-homo steroid synthesis.

Original language	English
Pages (from-to)	261-270
Number of pages	10
Journal	Steroids
Volume	29
Issue number	2
DOIs	https://doi.org/10.1016/0039-128X(77)90044-7
State	Published - Feb 1977

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title = "A steroid structure which refutes the isolation of C(17)-C(20) rotational isomers",

abstract = "Isolation of two C(17)-C(20) rotamers of 20-methyl-20-(2-hydroxy-ethoxy)-5-pregnene-3β, 17α-diol has been reported. X-Ray analysis of a diacetate derivative of one of the {"}rotamers{"} shows that the actual structure is 3β-acetoxy-17aα-(2-acetoxyethoxy)-17α,17aβ-dimethyl-D-homo-5-androsten-17β-ol (C28H44O6). Thus, although this investigation refutes the existence of C(17)-C(20) rotamers, it suggests a possible new pathway for D-homo steroid synthesis.",

author = "Weeks, \{Charles M.\} and Kruger, \{Gert J.\} and Duax, \{William L.\} and Makino Takuo and Osawa Yoshio",

year = "1977",

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journal = "Steroids",

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T1 - A steroid structure which refutes the isolation of C(17)-C(20) rotational isomers

AU - Weeks, Charles M.

AU - Kruger, Gert J.

AU - Duax, William L.

AU - Takuo, Makino

AU - Yoshio, Osawa

PY - 1977/2

Y1 - 1977/2

N2 - Isolation of two C(17)-C(20) rotamers of 20-methyl-20-(2-hydroxy-ethoxy)-5-pregnene-3β, 17α-diol has been reported. X-Ray analysis of a diacetate derivative of one of the "rotamers" shows that the actual structure is 3β-acetoxy-17aα-(2-acetoxyethoxy)-17α,17aβ-dimethyl-D-homo-5-androsten-17β-ol (C28H44O6). Thus, although this investigation refutes the existence of C(17)-C(20) rotamers, it suggests a possible new pathway for D-homo steroid synthesis.

AB - Isolation of two C(17)-C(20) rotamers of 20-methyl-20-(2-hydroxy-ethoxy)-5-pregnene-3β, 17α-diol has been reported. X-Ray analysis of a diacetate derivative of one of the "rotamers" shows that the actual structure is 3β-acetoxy-17aα-(2-acetoxyethoxy)-17α,17aβ-dimethyl-D-homo-5-androsten-17β-ol (C28H44O6). Thus, although this investigation refutes the existence of C(17)-C(20) rotamers, it suggests a possible new pathway for D-homo steroid synthesis.

UR - https://www.scopus.com/pages/publications/0017607691

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DO - 10.1016/0039-128X(77)90044-7

M3 - Article

C2 - 841624

AN - SCOPUS:0017607691

SN - 0039-128X

VL - 29

SP - 261

EP - 270

JO - Steroids

JF - Steroids

IS - 2

ER -

A steroid structure which refutes the isolation of C(17)-C(20) rotational isomers

Abstract

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