167893-02-9

Upstream product

• 167893-00-7 1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol 
• 143884-24-6 (5E,7E,20S)-3β-(tert-butyldimethylsilyloxy)-20-(p-tolylsulfonyloxymethyl)-9,10-seco-5,7,10(19)-pregnatriene 
• 167892-96-8 1α-hydroxy-3β-[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(E),7(E),10(19)-triene 
• 167892-97-9 1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(E),7(E),10(19)-triene 
• 167892-95-7 3β-[(t-butyldimethylsilyl)oxy]-20(S)-(propyl-23-oxo)-9,10-secopregna-5(E),7(E),10(19)-triene 
• 167892-94-6 (R)-4-{(1R,3aS,7aR)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentan-2-ol 
• 167892-92-4 3β-[(t-butyldimethylsilyl)oxy]-20(S)-(cyanomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene 
• 167892-93-5 3β-[(t-butyldimethylsilyl)oxy]-20(S)-(formylmethyl)-9,10-secopregna-5(E),7(E),10(19)-triene 
• 167892-98-0 (R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentan-2-ol 
• 167892-99-1 1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(Z),7(E),10(19)-triene 
• 143884-26-8 (5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene 

Downstream Products

• 286424-85-9 1α,3β-bis[(t-butyldimethylsilyl)oxy]-23(R)-[(methanesulfonyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol 
• 303015-21-6 (5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10⁽¹⁹⁾-cholestatrien-25-ol 
• 83805-11-2 Falecalcitriol 
• 210907-37-2 (6Z)-(3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5⁽¹⁰⁾,6,8-cholestatriene-3,25-diol-1-one 
• 210907-40-7 (6Z)-(1R,3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5(10),6,8-cholestatriene-1β,3β,25-triol 
• 163392-53-8 (5Z,7E)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-25-methoxymethoxy-9,10-seco-5,7,10⁽¹⁹⁾-cholestatriene 
• 303015-23-8 (5Z,7E)-(1S,3R,23R)-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-25-methoxymethoxy-9,10-seco-5,7,10⁽¹⁹⁾-cholestatrien-23-ol 
• 303015-22-7 (5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-25-methoxymethoxy-9,10-seco-5,7,10⁽¹⁹⁾-cholestatriene 
• 303015-24-9 (5Z,7E)-(1S,3R,23R)-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-25-methoxymethoxy-23-(methylthiothiocarbonyloxy)-9,10-seco-5,7,10⁽¹⁹⁾-cholestatriene 
• 286424-87-1 1α,3β-bis[(t-butyldimethylsilyl)oxy]-23(S),25-epoxy-26,26,26,27,27,27-hexafluoro-9,10-secocholesta-5(Z),7(E),10(19)-triene 

Relevant academic research and scientific papers

Synthesis and biological evaluations of A-ring isomers of 26,26,26,27,27,27-hexafluoro-1,25-dihydroxyvitamin D3

The activated vitamin D3 derivative 26,27-F6-1α,25(OH)2D3 (2a), its three A-ring diastereomers (2b, 2c, 2d), and 5,6-trans isomer (2e) were prepared. Two analogues (2b, 2c) of these isomers were synthesized by a palladium catalyzed coupling reaction using vinyl bromide 5 and enynes (6a, 6b), which were derived from readily commercially available 2S-(+)-glycidyl p-toluenesulfonate 7, as a common starting material. Competitive vitamin D receptor (VDR) binding affinities of these diastereomers of 2a were evaluated. Interestingly, the stereochemical effects at C-1,3 of 2a were considerably more moderate than those of 1α,25(OH)2D3 (1). In particular, isomerization at the 5,6-double bond of 2a only slightly reduced VDR affinity, whereas 5,6-trans-1α,25(OH)2D3 had a significantly lower binding affinity than 1. Copyright (C) 2000 Elsevier Science Ltd.

Synthesis and biological evaluations of C-23-modified 26,26,26,27,27,27-F6-vitamin D3 analogues

A convenient synthetic method which could allow flexible modification at C-23 of 26,26,26,27,27,27-hexafluoro-lα,25-dihydroxyvitamin D3 (3) has been developed. An effective construction of hexafluoroacetone (HFA) aldol part on the side chain of 10 was achieved by aldol reaction with HFA gas. This route is also attractive as an approach to diverse 26,27-modified vitamin D3 analogues. The preliminary biological activities of 23-modifed 26,27-F6 vitamin D3 analogues are evaluated. The potency of VDR affinities of the C-23-substituted analogues (keto group (4); OH group (5a,5b); fluorine atom (6a,6b); and oxetane ring (7a,7b)) was found to vary depending upon both the nature and stereochemistry of the substituents. In contrast, the HL-60 cell differentiation property was less varied than VDR affinity, and depended upon the nature rather than the stereochemistry of the substituents. Copyright (C) 2000 Elsevier Science Ltd.