122566-22-7

Basic information

• Product Name: (17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-ol
• Synonyms: (17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-ol;(17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-ol (Mixture of DiasteroMers);(172)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-ol (Mixture of Diasteromers)
• CAS NO: 122566-22-7
• Molecular Formula: C₂₈H₄₀O₅
• Molecular Weight: 456.6142
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 122566-22-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 607.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.20±0.1 g/cm3(Predicted)
• PKA: 14.20±0.60(Predicted)
• CAS DataBase Reference: (17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-ol(122566-22-7)
• EPA Substance Registry System: (17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-ol(122566-22-7)

Safety Data

• Hazardous Substances Data: 122566-22-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Powder

Uses

Like 17β-Estradiol (E888000) derivative, (17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-ol can be used in the preparation of Δ6-estrogens.

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 50-28-2 estradiol 
• 3589-91-1 3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene 

Downstream Products

• 1428627-89-7 4-{4-[6-((7α,17β)-3,17-dihydroxyestra-1,3,5(10)-trien-7-yl)-hex-1-ynyl]-phenyl}piperazine-1-carboxylic acid tert-butyl ester 
• 1428627-90-0 3,17β-bis(hydroxy)-7α-[6-(4-isoxazol-5-yl-phenyl)-hex-5-ynyl]estra-1,3,5(10)-triene 
• 1428627-91-1 3-{4-[6-((7α,17β)-3,17-dihydroxyestra-1,3,5(10)-trien-7-yl)hex-1-ynyl]phenyl}3-oxopropionic acid ethyl ester 
• 1428627-92-2 2-{4-[6-((7α,17β)-3,17-dihydroxyestra-1,3,5(10)-trien-7-yl)-hex-1-ynyl]-benzyl}malonic acid diethyl ester 
• 1428627-93-3 3,17β-bis(hydroxy)-7α-[6-(4-pyrrol-1-yl-phenyl)-hex-5-ynyl]estra-1,3,5(10)-triene 
• 1428627-94-4 3,17β-bis(hydroxy)-7α-[6-(4-piperidin-1-ylmethyl-phenyl)-hex-5-ynyl]-estra-1,3,5(10)-triene 
• 153004-31-0 (+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol 
• 862700-70-7 3,17β-bis(2-tetrahydropyranyloxy)-7α-[9-(4,4,5,5,5-pentafluoropentyl)thiononyl]estra-1,3,5(10)-triene-6-one 
• 129453-61-8 fulvestrant 
• 571-92-6 6-ketoestradiol 
• 7291-41-0 6-Dehydroestradiol 
• 251322-18-6 7α-(15-benzyloxy-7,10,13-trioxapentadecan-1-yl)-17β-(t-butyldimethylsilanyloxy)-3-(2-methoxyethoxymethoxy)estra-1,3,5(10)-triene 
• 251322-05-1 7α-[6-(S-benzoylthio)hexan-1-yl]-3,17β-bis(t-butyldimethylsilanyloxy)estra-1,3,5(10)-triene 
• 251322-26-6 3-(benzyloxy)-7α-(6-benzyloxy-4-oxahexan-1-yl)-17β-(t-butyldimethylsilanyloxy)estra-1,3,5(10)-triene 

Relevant articles and documents

Synthesis of novel estrogen receptor antagonists using metal-catalyzed coupling reactions and characterization of their biological activity

Estrogen receptor (ER) antagonists are valuable in the treatment of ER-positive human breast cancer. In this study, we designed and synthesized nine new derivatives of 17β-estradiol (E2) with a bulky side chain attached to its C-7α position, and determined their ER antagonistic activity using in vitro bioassays. Four of the derivatives showed a strong inhibition of ERα transactivation activity in a luciferase reporter assay and blocked ERα interactions with coactivators. Similarly, these derivatives also strongly inhibited the growth of the ERα-positive human breast cancer cells. Computational docking analysis was conducted to model the interaction of these antagonists with the human ERα and showed that they could tightly bind to the ERα in a manner similar to that of ICI-182,780, a pure ER antagonist. These results provide an example that attachment of a bulky side chain to the C-7α position of E2 can produce ER antagonists with ER affinity comparable to that of ICI-182,780.

Process for the manufacture of 7-alpha-[9-(4,4,5,5,5-penta fluoropentylsulphinyl) nonyl]estra-1,3,5-(10)- triene-3,17-beta-diol

The present invention provides a novel multi-step process for the manufacturing Fulvestrant, which is economical and convenient to operate at commercial scale, and requires only simple chromatographic separations after the coupling step of adding the side chain to the 7 position of the steroid.

C6-(N,N-butyl-methyl-heptanamide) derivatives of estrone and estradiol as inhibitors of type 1 17β-hydroxysteroid dehydrogenase: Chemical synthesis and biological evaluation

A series of estrone and estradiol derivatives having an N-butyl,methyl heptanamide side chain at C6-position were synthesized, tested as inhibitors of type 1 17β-HSD and assessed for their possible estrogenic activity. A better type 1 17β-HSD inhibition w