153277-34-0

Basic information

• Product Name: Carbamic acid, [1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-(phenylthio)ethyl]-, phenylmethyl ester, (R)-
• CAS NO: 153277-34-0
• Molecular Formula: C23H33NO3SSi
• Molecular Weight: 431.671
• Mol File: 153277-34-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-(phenylthio)ethyl]-, phenylmethyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-(phenylthio)ethyl]-, phenylmethyl ester, (R)-(153277-34-0)
• EPA Substance Registry System: Carbamic acid, [1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-(phenylthio)ethyl]-, phenylmethyl ester, (R)-(153277-34-0)

Safety Data

• Hazardous Substances Data: 153277-34-0(Hazardous Substances Data)

Upstream product

• 930-69-8 sodium thiophenolate 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 153277-22-6 (R)-benzyl (1-hydroxy-3-(phenylthio)propan-2-yl)carbamate 
• 82611-65-2 N-benzyloxycarbonyl-S-phenyl-L-cysteine 
• 132249-34-4 Methyl (S)-2-benzyloxycarbonylamino-3-methylsulfonyloxypropanoate 
• 153277-33-9 N-benzyloxycarbonyl-S-phenyl-L-cysteine methyl ester 

Downstream Products

• 153379-64-7 O-Deacetyl-N-(benzyloxycarbonyl)slaframine 
• 153277-29-3 ((1S,6S,8aS)-1-Methoxymethoxy-octahydro-indolizin-6-yl)-carbamic acid benzyl ester 
• 153379-66-9 (1S,6S,8aS)-6-(benzyloxycarbonylamino)octahydroindolizin-1-yl acetate 
• 153277-31-7 (2S,3S)-2-((S)-3-Benzyloxycarbonylamino-4-hydroxy-butyl)-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 153277-32-8 (2S,3S)-2-((S)-3-Benzyloxycarbonylamino-4-methanesulfonyloxy-butyl)-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 153277-28-2 (2S,3S,3'S)-2-<4'-(tert-Butyldimethylsilyloxy)-3'-(benzyloxycarbonylamino)butyl>-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine 
• 153277-26-0 (2S,3S,1'S,2'R,3'R)-1-(tert-Butoxycarbonyl)-2-<3'-benzyloxycarbonylamine-4'-(tert-butyldimethylsilyloxy)-1'-hydroxy-2'-phenylsulfonylbutyl>-3-(methoxymethoxy)pyrrolidine 
• 153277-27-1 (2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 153277-21-5 (R)-2-Benzyloxycarbonylamino-1-(tert-butyldimethylsilyloxy)-3-phenylsulfonylpropane 

Relevant articles and documents

Total synthesis of (-)-slaframine from (2R,3S)-3-hydroxyproline

The yeast reduction products (2R,3S)-N-Boc-3-hydroxyproline esters 23 have been converted into the 3-methoxymethoxyprolinal 26 which undergoes an efficient Julia olefination with the L-serine-derived amino sulfone 29. Selective reduction of the resulting alkene 31 using diimide and cyclization leads to N-(benzyloxycarbonyl)slaframine 33c and thence to natural (-)-slaframine 5 and its more stable, crystalline N-acetyl derivative 34.