ISSN:
0170-2041
Keywords:
5β-Pregnane, 3α-hydroxy-20-one
;
Chiral borane reduction
;
Borane reduction
;
Steroids
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The direction of reduction of 20-carbonyl group of 3α-hydroxy-5β-pregnan-20-one (1) with a complex of borane-methyl sulfide and chiral β-amino alcohols, depends on the chirality of the amino alcohol. Where there is a 2-phenyl or 2-benzyl substituent, then the S enantiomer gives exclusively the steroid 20R alcohol 3. The R enantiomer of 2-amino-2-phenyl-1-ethanol gives the highest steroid 20S (2):20R (3) alcohol ratio.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199319930194
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