81522-68-1

Basic information

• Product Name: PHOSPHINE OXIDE, [2-[3,5-BIS [[(1,1-DIMETHYLETHYL) DIMETHYLSILY]OXY]-2-METHYLENECYCLOHEXYLIDENE]ETHYL]DIPHENYL-,[3S-(1Z,3A,5B0)]
• Synonyms: PHOSPHINE OXIDE, [2-[3,5-BIS [[(1,1-DIMETHYLETHYL) DIMETHYLSILY]OXY]-2-METHYLENECYCLOHEXYLIDENE]ETHYL]DIPHENYL-,[3S-(1Z,3A,5B0)];3S-(1Z,3A,5B)]-[2-[3,5-BIS[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]-2-METHYLENE-CYCLOHEXYLIDENE]-ETHYL]DIPHENYL-PHOSPHINE OXIDE;INTERMEDIATEFORVITAMIND;[3S-(1Z,3a,5b)]-[2-[3,5-Bis[[(tert-butyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphineoxide;[3S-(1Z;1-diMethylethyl)-diMethylsilyl]-oxy}-2-Methylenecyclohexylidene}-ethyl] -diphenyl phosphine oxide;5b)]-[2-{3;5-bis-{[(1
• CAS NO: 81522-68-1
• Molecular Formula: C₃₃H₅₁O₃PSi₂
• Molecular Weight: 582.909
• Mol File: 81522-68-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 571.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.02±0.1 g/cm3(Predicted)
• CAS DataBase Reference: PHOSPHINE OXIDE, [2-[3,5-BIS [[(1,1-DIMETHYLETHYL) DIMETHYLSILY]OXY]-2-METHYLENECYCLOHEXYLIDENE]ETHYL]DIPHENYL-,[3S-(1Z,3A,5B0)](CAS DataBase Reference)
• NIST Chemistry Reference: PHOSPHINE OXIDE, [2-[3,5-BIS [[(1,1-DIMETHYLETHYL) DIMETHYLSILY]OXY]-2-METHYLENECYCLOHEXYLIDENE]ETHYL]DIPHENYL-,[3S-(1Z,3A,5B0)](81522-68-1)
• EPA Substance Registry System: PHOSPHINE OXIDE, [2-[3,5-BIS [[(1,1-DIMETHYLETHYL) DIMETHYLSILY]OXY]-2-METHYLENECYCLOHEXYLIDENE]ETHYL]DIPHENYL-,[3S-(1Z,3A,5B0)](81522-68-1)

Safety Data

• Hazardous Substances Data: 81522-68-1(Hazardous Substances Data)

Usage

Uses

[(2Z)-2-[(3S,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine Oxide is used as a reagent in the preparation of hydroxymethylated dihydroxyvitamin D3 analogs which have antitumor and transactivation activity.

Upstream product

• 81506-25-4 <3S-(1Z,3α,5β)>-2-<3,5-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>-1-chloroethane 
• 4559-70-0 Diphenylphosphine oxide 
• 65567-06-8 lithium diphenylphosphide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 81570-20-9 <3S-(1Z,3α,5β)>-<3,5-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetic acid ethyl ester 
• 81506-17-4 <2S-(1E,2α,3β,5α)>-<2-(acetyloxy)-3-hydroxy-2-methyl-5-(1-methylethenyl)cyclohexylidene>acetic acid ethyl ester 
• 342645-70-9 ethyl (5S,7S)-5,7-bis[(1,1-dimethylethyl)dimethylsilyloxy]-3-oxo-8-nonenate 
• 829-85-6 diphenylphosphane 
• 172516-23-3 (3S,5S)-3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-6-heptenal 
• 161678-01-9 (S)-6-chloro-5-hydroxy-1-hexen-3-one 
• 342645-69-6 (3R,5S)-3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-6-heptenitrile 
• 342644-77-3 (3R,5S)-3,5-dihydroxy-6-heptenitrile 
• 442518-51-6 ethyl 2-[(1S,4S,6S)-1-methyl-7-oxa-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-bicyclo[4.1.0]hept-2-ylidene]acetate 
• 326496-90-6 (1S,4S,6S)-4-(1-acetylhydroperoxy-1-methoxyethyl)-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one 

Downstream Products

• 60133-18-8 ercalcitriol 
• 157380-23-9 (1R,3aR,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-7a-methyl-octahydro-indene 
• 181116-83-6 (R)-6-{(S)-3-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-methyl-cyclohexyl}-5-methyl-hept-6-enoic acid methyl ester 
• 163379-71-3 (1S,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-[2-[(S)-3-[(1R,2R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1,2,6-trimethyl-heptyl]-3-methyl-cyclohex-(E)-ylidene]-eth-(Z)-ylidene]-2-methylene-cyclohexane 
• 181116-72-3 (1S,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-3-[2-[(S)-3-methyl-3-((1R,2R)-1,2,6-trimethyl-6-triethylsilanyloxy-heptyl)-cyclohex-(E)-ylidene]-eth-(Z)-ylidene]-cyclohexane 
• 198277-63-3 (R)-5-{(1R,3aR,7aR)-4-[2-[(3S,5R)-3,5-Dihydroxy-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-yl}-hexanal 
• 217470-08-1 (20S)-1α-<(tert-butyldimethylsilyl)oxy>-16-en-25-<(methoxymethyl)oxy>vitamin D₃ tert-butyldimethylsilyl ether 
• 217470-03-6 (3aS,7aS)-7-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-3-((S)-1-cyclopropyl-5-methoxymethoxy-5-methyl-hexyl)-3a-methyl-3a,4,5,6,7,7a-hexahydro-1H-indene 
• 217470-01-4 (20S)-1α-<(tert-butyldimethylsilyl)oxy>-16-en-25-<(methoxymethyl)oxy>-21-propylvitamin D₃ tert-butyldimethylsilyl ether 
• 197647-58-8 (1R,3aS,7aS)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-isopropyl-7a-(4-methyl-4-trimethylsilanyloxy-pentyloxymethyl)-octahydro-indene 
• 197647-52-2 (1R,3aS,7aS)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-isopropyl-7a-(5-methyl-5-trimethylsilanyloxy-hexyloxymethyl)-octahydro-indene 
• 228420-89-1 (17E)-1α-<(tert-butyldimethylsilyl)oxy>-16α-<(2',2'-dimethylpropanoyl)oxy>-17(20)-en-25-<(methoxymethyl)oxy>vitamin D₃ tert-butyldimethylsilyl ether 
• 228420-96-0 2,2-Dimethyl-propionic acid (2R,3aS,7aS)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-[5-methoxymethoxy-5-methyl-hex-(Z)-ylidene]-7a-methyl-octahydro-inden-2-yl ester 
• 220173-61-5 (1R,3aS,7aS)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-isopropyl-7a-(5-methyl-5-trimethylsilanyloxy-hex-2-ynyloxymethyl)-octahydro-indene 

Relevant articles and documents

PROCESS FOR PRODUCING PHOSPHINE OXIDE VITAMIN D PRECURSORS

A process for producing a compound of the formula: including reacting of a compound of the formula: with diphenyl phosphine oxide using a binary phase reaction mixture including diphenyl phosphine oxide in an organic solvent, a basic aqueous solution, and a phase transfer catalyst, to obtain the compound of formula 1, wherein Ph is phenyl, X1 and X2 are both hydrogen or X1 and X2 taken together are CH2, R1 is a protecting group, R2 is fluorine, hydrogen, or OR3, wherein R3 is a protecting group, and the squiggly line represents a bond that results in the adjacent double bond being in either the E or Z configuration, is disclosed.

Improved preparation of A-ring phosphine oxides for the synthesis of vitamin D analogs

A new, high yielding, two-step process for the preparation of A-ring phospine oxides from allyl alcohols, useful for the synthesis of vitamin D analog, is described, in which triphos-gene and diphenylphosphine oxide are used for chlorination and subsequen

Parallel synthesis of a vitamin D3 library in the solid-phase

A highly efficient synthesis of the vitamin D3 system on solid support is described. Two synthetic strategies for the solid-phase synthesis of vitamin D3 were developed. One is for 11-hydroxy analogues, and the other is for most other synthetic analogues. In the latter strategy, the sulfonate-linked CD-ring 58 was initially immobilized on PS-DES resin to give solid-supported CD-ring 63 (Scheme 10). Similarly, solid-supported CD-ring 63 was prepared by attachment of the CD-ring 10 to the chlorosulfonate resin 64. The vitamin D3 system was synthesized by Horner-Wadsworth-Emmons reaction of the A-ring phosphine oxide to a solid-supported CD-ring, followed by simultaneous introduction of the side chain and cleavage from resin with a Cu1-catalyzed Grignard reagent. Parallel synthesis of the vitamin D3 analogues was accomplished by a split and pool methodology utilizing radio frequency encoded combinatorial chemistry, and a manual parallel synthesizer for side chain diversification and deprotection. Additionally, we demonstrated the synthesis of various A-rings in a similar protocol for efficient preparation of building blocks.