198009-73-3

Basic information

• Product Name: [(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-heptadec-3-enyl]-carbamic acid tert-butyl ester
• Synonyms: [(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-heptadec-3-enyl]-carbamic acid tert-butyl ester
• CAS NO: 198009-73-3
• Molecular Weight: 752.282
• Mol File: 198009-73-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-heptadec-3-enyl]-carbamic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-heptadec-3-enyl]-carbamic acid tert-butyl ester(198009-73-3)
• EPA Substance Registry System: [(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-heptadec-3-enyl]-carbamic acid tert-butyl ester(198009-73-3)

Safety Data

• Hazardous Substances Data: 198009-73-3(Hazardous Substances Data)

Upstream product

• 198009-70-0 [(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-carbamic acid tert-butyl ester 
• 198009-75-5 [(1S,2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-butyl]-carbamic acid tert-butyl ester 
• 198009-71-1 [(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 198009-69-7 (2S,3R,4R)-2-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3,4-dihydroxy-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 198009-74-4 [(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester 
• 157809-42-2 (S)-2-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 
• 161791-59-9 [(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-formyl-ethyl]-carbamic acid tert-butyl ester 
• 141293-15-4 (1'S,2R,4''R)-2-[(2,2-dimethyl-[1,3]dioxolan-4-yl)hydroxymethyl]-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester 
• 141293-28-9 N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole 

Downstream Products

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 

Relevant articles and documents

Diastereoselective synthesis of D-erythro-sphingosine

A twelve-step, diastereoselective synthesis of D-erythro-C18-sphingosine [(2S,3R,4E)-2-amino-1,3-dihydroxy-4-octadecene, 1] is described (12 steps, 10% overall yield), starting from 2,3-O-isopropylidene-D-glyceraldehyde 3. The first step was the crossed addition of N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsilyloxy)pyrrole (TB-SOP, 2) to 2,3-O-isopropylidene-D-glyceraldehyde 3 (a vinylogous variant of the Mukaiyama-aldol reaction) producing a seven-carbon lactam intermediate 4, which was then shortened by three carbon atoms to furnish the aldehydo-erythrose derivative 10. Wittig elongation of 10 with the appropriate C14 ylide, followed by photoinduced Z to E double bond isomerization and removal of the protecting groups, completed the synthesis.