3747-91-9

Basic information

• Product Name: Dehydroepianderosterone TMS
• Synonyms: 3β-(Trimethylsiloxy)androst-5-en-17-one;Dehydroepianderosterone TMS
• CAS NO: 3747-91-9
• Molecular Formula: C22H36O2Si
• Molecular Weight: 360.60554
• Mol File: 3747-91-9.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Dehydroepianderosterone TMS(CAS DataBase Reference)
• NIST Chemistry Reference: Dehydroepianderosterone TMS(3747-91-9)
• EPA Substance Registry System: Dehydroepianderosterone TMS(3747-91-9)

Safety Data

• Hazardous Substances Data: 3747-91-9(Hazardous Substances Data)

Upstream product

• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 53-43-0 dehydroepiandrosterone 
• 75-77-4 chloro-trimethyl-silane 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 2283-82-1 3α-hydroxy-androst-5-en-17-one 
• 81-07-2 saccharin 

Downstream Products

• 3604-60-2 17alpha-ethynyl-3beta,17beta-dihydroxy-androst-5-ene 
• 124643-35-2 C₂₀H₂₇F₃O₄S 
• 154229-19-3 abiraterone 
• 154229-18-2 abiraterone acetate 

Relevant articles and documents

Carbonyl-Directed Aliphatic Fluorination: A Special Type of Hydrogen Atom Transfer Beats out Norrish II

Recently, our group reported that enone and ketone functional groups, upon photoexcitation, can direct site-selective sp3 C-H fluorination in terpenoid derivatives. How this transformation actually occurred remained mysterious, as a significant number of mechanistic possibilities came to mind. Herein, we report a comprehensive study describing the reaction mechanism through kinetic studies, isotope-labeling experiments, 19F NMR, electrochemical studies, synthetic probes, and computational experiments. To our surprise, the mechanism suggests intermolecular hydrogen atom transfer (HAT) chemistry is at play, rather than classical Norrish hydrogen atom abstraction as initially conceived. What is more, we discovered a unique role for photopromoters such as benzil and related compounds that necessitates their chemical transformation through fluorination in order to be effective. Our findings provide documentation of an unusual form of directed HAT and are of crucial importance for defining the necessary parameters for the development of future methods.

Methods of preparing pharmaceutical solid state forms

The invention provides and describes solid state 17α-ethynyl-5α-androstane-3α,17β-diol including amorphous and crystalline forms and specific polymorphic forms thereof. Anhydrates and solvates of 17α-ethynyl-5α-androstane-3α,17β-diol include Form III anhydrate and Form I solvate. The invention further relates to solid and suspension formulations containing 17α-ethynyl-5α-androstane-3α,17β-diol in a described solid state form and use of the formulations to treat cancers or precancers such as prostate cancer or breast cancer in subjects or human patients. The invention also relates to methods to make liquid formulations from solid state forms of 17α-ethynyl-5α-androstane-3α,17β-diol and uses of such formulations in treating the described conditions.

METHODS AND COMPOUNDS FOR PREPARING 3ALPHA-OXYGEN SUBSTITUTED STEROIDS

The invention relates to processes for preparing 3α-O-linked steroids including 3α-O-linked-androst-5-ene steroids and 3α-O-linked-5a-androstane steroids. In one process a 3α,4α-epoxy androst-5-en-17-one is predominately reduced at the epoxy moiety wherein reduction of the 3α,4α epoxy functional group occurs preferentially at position C4 with retention of configuration at position C3 to provide a 3α-O-linked-androst-5-ene steroid. In another process, conditions are provided for inversion of configuration of a 3β-hydroxy-androst-5-ene steroid by the Mitsunobu reaction to provide a 3α-O-linked-androst-5-ene steroid with reduced amounts of 3α,5α-cycloandrostane side-product impurities.