327048-83-9

Upstream product

• 327049-03-6 2,3,4-13C3-17β-tert-butyldimethylsilyloxy-4,5-seco-1-androsten-3,5-dione 
• 327049-08-1 2,3,4-13C3-17β-tert-butyldimethylsilyloxy-4,5-seco-androstan-3,5-dione 
• 327049-05-8 2,3,4-13C3-17β-tert-butoxy-4,5-seco-1-androsten-3,5-dione 
• 327049-09-2 2,3,4-13C3-17β-tert-butoxy-4,5-seco-androstan-3,5-dione 
• 327048-81-7 2,3,4-13C3-17β-hydroxy-4,5-seco-1-androsten-3,5-dione 
• 327048-89-5 17β-tert-butyldimethylsilyloxy-2-oxaandrost-4-en-3-one 
• 327049-06-9 2,3,4-13C₃-4,5-seco-1-androsten-3,5,17-trione 
• 327048-93-1 17β-tert-butyldimethylsilyloxy-1-hydroxy-1,5-secoandrostan-5-one 
• 327049-10-5 2,3,4-13C₃-4,5-seco-androstan-3,5,17-trione 
• 327048-96-4 17β-tert-butyldimethylsilyloxy-10-formyl-des-A-androstan-5-one 
• 327048-91-9 17β-tert-butoxy-2-oxaandrost-4-en-3-one 
• 327048-78-2 1,17β-dihydroxy-1,5-secoandrostan-5-one 
• 326864-25-9 17β-hydroxy-10-formyl-5-oxo-des-A-androstane 
• 327048-99-7 10-formyl-des-A-androstan-5,17-dione 

Relevant academic research and scientific papers

Novel partial synthetic approaches to replace carbons 2,3,4 of steroids. A methodology to label testosterone and progesterone with 13C in the steroid A ring. Part 2

Fragmentation of the A ring of the steroid hormone testosterone to yield the 10-formyl-5-oxo-des A intermediate was achieved by lactolization, lactonization, ozonolysis, and oxidation of the resulting methylol group. The reconstruction of the A ring was carried out via a Wittig synthesis with triphenylphosphoranylidene-2-propanone-13C3. Syntheses of the ylide, of the 13C3-testosterone, and of 13C3-progesterone took place in acceptable yields. (C) 2000 Elsevier Science Ltd.

Synthesis of labelled [13C6]testosterone and [13C5]19-nortestosterone

The condensation of ethyl acetoacetate-13C4 and ethyl bromoacetate-13C2 afforded, in seven steps, (1,2,3,4,5-13C5) 5-(diethylphosphono)-2-pentanone ethylene ketal 9. The reaction of this labelled compound with 7-[[(1,1-dimethylethyl)-dimethylsilyl]oxy]-1,6,6a,7,8, 9, 9a, 9b-octahydro-6a-methyl-[6aS-(6aa,7a,9aβ,9ba)] cyclopenta[f][1]benzopyran-3 (2H)-one 13 gave the benzindenone 14 which was converted to (1,2,3,4,10,19-13C6)testosterone 17 then, into (1,2,3,4,10-13C5)19-nortestosterone 18 by a reductive alkylation method.

[1,2,3,4-13C] testosterone and [1,2,3,4-13C] estradiol

The preparation of [1,2,3,4-13C] testosterone and of [1,2,3,4-13C] estradiol by total synthesis is described. The 13C labels are introduced by alkylating intermediate 1 with [1,2,3,4-13C]l-iodo-3,3-ethylenedioxybutane (2) to obtain intermediate 10. Hydrolysis of the ketal function, cyclization, aromatization and removal of protective groups gave [1,2,3,4-13C] estradiol. Labeled testosterone was prepared by methylating intermediate 10 and by subsequent treatment with acid. The labeled steroids can be used as tracers for in vivo metabolic studies and as internal standards for the development of definitive gc-ms quantitative methods.