Mass spectral determination of the configuration of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol

S. Di-Capua; H. G. Jang; D. Barasch; G. Halperin; J. Deutsch

doi:10.1016/s0168-1176(97)00034-7

Mass spectral determination of the configuration of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol

S. Di-Capua, H. G. Jang, D. Barasch, G. Halperin, J. Deutsch^*

^*Corresponding author for this work

School of Pharmacy

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

2 Scopus citations

Abstract

The stereochemistry of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol was determined by mass spectral measurements of the extent of water elimination from the molecular ion under electron impact conditions. The [M-H₂O]⁺/[M]^.+ ratio of the 3β-OH isomer was found to be three to four times higher than that of the 3α-OH isomer. The 3α-OH isomer produced a crystalline 3α-benzyloxy derivative; its configuration and stereochemistry of the steroidal rings were determined by X-ray crystallography. The 3α-OH isomer was obtained by reduction of the corresponding carbonyl group with NaBH₄. The 3β-OH isomer was synthesized by Walden inversion of the 3α-OH isomer. The 3β configuration of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol was also supported by its ability to bind digitonin.

Original language	English
Pages (from-to)	79-85
Number of pages	7
Journal	International Journal of Mass Spectrometry and Ion Processes
Volume	167-168
DOIs	https://doi.org/10.1016/s0168-1176(97)00034-7
State	Published - 1997

Keywords

Electron impact
Mass spectrometry
Stereochemistry
Steroids

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10.1016/s0168-1176(97)00034-7

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@article{4d4355c032cd440eb88bfcb2aa5b19d4,

title = "Mass spectral determination of the configuration of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol",

abstract = "The stereochemistry of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol was determined by mass spectral measurements of the extent of water elimination from the molecular ion under electron impact conditions. The [M-H2O]+/[M].+ ratio of the 3β-OH isomer was found to be three to four times higher than that of the 3α-OH isomer. The 3α-OH isomer produced a crystalline 3α-benzyloxy derivative; its configuration and stereochemistry of the steroidal rings were determined by X-ray crystallography. The 3α-OH isomer was obtained by reduction of the corresponding carbonyl group with NaBH4. The 3β-OH isomer was synthesized by Walden inversion of the 3α-OH isomer. The 3β configuration of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol was also supported by its ability to bind digitonin.",

keywords = "Electron impact, Mass spectrometry, Stereochemistry, Steroids",

author = "S. Di-Capua and Jang, {H. G.} and D. Barasch and G. Halperin and J. Deutsch",

year = "1997",

doi = "10.1016/s0168-1176(97)00034-7",

language = "אנגלית",

volume = "167-168",

pages = "79--85",

journal = "International Journal of Mass Spectrometry and Ion Processes",

issn = "0168-1176",

publisher = "Elsevier B.V.",

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T1 - Mass spectral determination of the configuration of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol

AU - Di-Capua, S.

AU - Jang, H. G.

AU - Barasch, D.

AU - Halperin, G.

AU - Deutsch, J.

PY - 1997

Y1 - 1997

N2 - The stereochemistry of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol was determined by mass spectral measurements of the extent of water elimination from the molecular ion under electron impact conditions. The [M-H2O]+/[M].+ ratio of the 3β-OH isomer was found to be three to four times higher than that of the 3α-OH isomer. The 3α-OH isomer produced a crystalline 3α-benzyloxy derivative; its configuration and stereochemistry of the steroidal rings were determined by X-ray crystallography. The 3α-OH isomer was obtained by reduction of the corresponding carbonyl group with NaBH4. The 3β-OH isomer was synthesized by Walden inversion of the 3α-OH isomer. The 3β configuration of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol was also supported by its ability to bind digitonin.

AB - The stereochemistry of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol was determined by mass spectral measurements of the extent of water elimination from the molecular ion under electron impact conditions. The [M-H2O]+/[M].+ ratio of the 3β-OH isomer was found to be three to four times higher than that of the 3α-OH isomer. The 3α-OH isomer produced a crystalline 3α-benzyloxy derivative; its configuration and stereochemistry of the steroidal rings were determined by X-ray crystallography. The 3α-OH isomer was obtained by reduction of the corresponding carbonyl group with NaBH4. The 3β-OH isomer was synthesized by Walden inversion of the 3α-OH isomer. The 3β configuration of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol was also supported by its ability to bind digitonin.

KW - Electron impact

KW - Mass spectrometry

KW - Stereochemistry

KW - Steroids

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SN - 0168-1176

VL - 167-168

SP - 79

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JO - International Journal of Mass Spectrometry and Ion Processes

JF - International Journal of Mass Spectrometry and Ion Processes

ER -

Mass spectral determination of the configuration of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol

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Keywords

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