342644-90-0

Basic information

• Product Name: [3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate
• Synonyms: [3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate
• CAS NO: 342644-90-0
• Molecular Weight: 498.851
• Mol File: 342644-90-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: [3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: [3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate(342644-90-0)
• EPA Substance Registry System: [3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate(342644-90-0)

Safety Data

• Hazardous Substances Data: 342644-90-0(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 168109-89-5 (1R)-1-((4R,5R)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol 
• 4239-90-1 (4S,4'R,5R)-2,2,2',2'-tetramethyl-5-vinyl-4,4'-bi(1,3-dioxolane) 
• 38145-93-6 1,2:3,4-di-O-isopropylidene-D-mannitol 
• 3969-59-3 mannitol triacetonide 
• 69-65-8 mannitol 
• 342644-83-1 [3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethyl trimethylacetate 
• 244278-87-3 [3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethanol 
• 3282-30-2 pivaloyl chloride 
• 377091-68-4 [3R-(1Z,3β,4α,5α)]-2-[3,4,5-trihydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate 

Downstream Products

• 342645-82-3 [3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]-1-chloroethane 
• 200636-54-0 [3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide 
• 200636-50-6 [3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]-1-chloroethane 
• 104121-92-8 Eldecalcitol 
• 342645-84-5 (1β,2α,3α,5Z,7E)-1,3-bis[(1,1-dimethylethyl)dimethylsilyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-25-trimethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene 
• 342645-07-2 (1α,2β,3β,5Z,7E,20S)-1,3-bis[(1,1-dimethylethyl)dimethyl-silyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-9,10-secopregna-5,7,10(19)-triene-20-methyl 4-methylbenzenesulfonate 

Relevant articles and documents

Structural revisions of the reported A-ring phosphine oxide synthon for ED-71 (Eldecalcitol) and a new synthesis

In a reported procedure for the synthesis of the ED-71 A-ring phosphine oxide, we discovered that unusual TBS transfer occurred from the 1α-position to the sterically more constrained 2β-position, and the subsequent Michael addition of ethyl acrylate predominated at the 1α-position. The X-ray analysis of a key intermediate confirmed our observations. We made a structural revision of the reported A-ring phosphine oxide synthon and ED-71. In addition, we provided the first stereoselective synthetic approach to ED-71 A-ring phosphine oxide applying the stereochemistry of d-mannitol.