PMID: 9185293Jun 1, 1997Paper

An efficient stereoselective synthesis of 6-alpha-aminoestradiol: preparation of estradiol fluorescent probes

Steroids
M AdamczykR E Reddy

Abstract

6-Oxoestradiol (2) was protected as its bis[(2-trimethylsilylethoxy)methyl] ether (4) and converted to the corresponding oxime (4). The oxime (4) on reduction with zinc in ethanol afforded the bis-SEM ether of 6-alpha-aminoestradiol (5) in 96% epimeric excess. Subsequently, 5 was hydrolyzed with HF to 6-alpha-aminoestradiol (6) in good yield. The absolute stereochemistry of the amino group in 6 was established by NMR and confirmed by X-ray crystallography on the corresponding 4-bromobenzamide derivative (9). Treatment of amine (6) with 6-(t-butoxycarbonylamino)hexanoic acid succinimidyl ester (10) followed by hydrolysis produced the amine (12) with a C-6 linker. The fluorescent probes (7 and 13) were prepared from 6 and 12 respectively, in 54-60% yield and > 99% purity.

References

Dec 19, 1979·Biochimica Et Biophysica Acta·D P EdwardsW L McGuire
Oct 26, 1978·The New England Journal of Medicine·M E Lippman, J C Allegra
Jan 24, 1977·Biochemical and Biophysical Research Communications·W B DandlikerR J Brawn
May 1, 1990·Journal of Steroid Biochemistry·L X Tiefenauer, R Y Andres
Dec 1, 1989·Journal of Steroid Biochemistry·D M BodmerR Y Andres
Feb 1, 1989·Journal of Steroid Biochemistry·L X TiefenauerR Y Andres
Nov 1, 1982·European Journal of Cancer & Clinical Oncology·B G JoyceK Griffiths
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Jan 1, 1987·Journal of Pharmaceutical and Biomedical Analysis·A M Johnson

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Citations

Apr 20, 2002·Bioorganic & Medicinal Chemistry Letters·Maciej AdamczykZhiguang Yu
Mar 5, 2002·Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry·Tomoyuki OeToshimasa Toyo'oka
Feb 10, 2019·Steroids·Nisal Gajadeera, Robert N Hanson

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