154161-00-9

Basic information

• Product Name: (1S,2S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-hydroxypent-4-enyl]carbamic acid benzyl ester
• Synonyms: (1S,2S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-hydroxypent-4-enyl]carbamic acid benzyl ester
• CAS NO: 154161-00-9
• Molecular Weight: 379.572
• Mol File: 154161-00-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1S,2S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-hydroxypent-4-enyl]carbamic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-hydroxypent-4-enyl]carbamic acid benzyl ester(154161-00-9)
• EPA Substance Registry System: (1S,2S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-hydroxypent-4-enyl]carbamic acid benzyl ester(154161-00-9)

Safety Data

• Hazardous Substances Data: 154161-00-9(Hazardous Substances Data)

Upstream product

• 154161-05-4 L-N-(benzyloxycarbonyl)-O-<(1,1-dimethylethyl)dimethylsilyloxy>serine methyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 154161-01-0 [(2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-ethyl]-carbamic acid benzyl ester 
• 762-72-1 allyl-trimethyl-silane 
• 154659-09-3 (R)-benzyl (1-((tert-butyldimethylsilyl)oxy)-3-hydroxypropan-2-yl)carbamate 

Downstream Products

• 154278-84-9 (2R,3R)-2-(hydroxymethyl)-3-hydroxypyrrolidine hydrochloride 
• 154161-04-3 (2R,3S)-2-Formyl-3-triisopropylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester 
• 220198-02-7 (1S,2S)-[1-(benzyloxymethyl)-2-hydroxypent-4-enyl]carbamic acid benzyl ester 
• 468061-03-2 (1S,2S,4SR)-[1-(tert-butyldimethylsilanyloxymethyl)-4,5-dihydroxy-2-triisopropylsilanyloxypentyl]carbamic acid benzyl ester 
• 154160-99-3 (1S,2S)-[1-(tert-butyldimethylsilanyloxymethyl)-4-oxo-2-triisopropylsilanyloxybutyl]carbamic acid benzyl ester 
• 468061-04-3 (2S,3S)-2-(tert-butyldimethylsilanyloxymethyl)-3-triisopropylsilanyloxypyrrolidine-1-carboxylic acid benzyl ester 
• 154161-03-2 (2R,3S)-3-triisopropylsilanyloxypyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 
• 154161-02-1 (2S,3S)-2-(hydroxymethyl)-3-triisopropylsilanyloxypyrrolidine-1-carboxylic acid benzyl ester 
• 174389-11-8 (2R,3S)-N-(benzyloxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid 
• 350592-84-6 cis-3-hydroxy-D-prolinol 
• 138515-34-1 (2S,3S)-1-(Benzyloxycarbonyl)-3-hydroxy-2-(hydroxymethyl)pyrrolidine 
• 123411-86-9 (1S,2S)-(2-hydroxy-1-hydroxymethylpent-4-enyl)carbamic acid benzyl ester 
• 468061-02-1 (1S,2S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-triisopropylsilanyloxypent-4-enyl]carbamic acid benzyl ester 
• 119593-44-1 (2R,3S)-3-hydroxypipecolic acid 

Relevant articles and documents

Highly Stereoselective Synthesis of cis-(2R,3S)-3-Hydroxyproline

Allyltrimethylsilane (5) reacted with N-carbobenzoxy-O-tert-butyldimethylsilyl-L-serinal (4) to give with high diastereoselectivity syn-adduct 3 which was subsequently transformed into cis-(2R,3S)-3-hydroxyproline (1).

The stereochemical course of addition of allyltrimethylsilane to protected L-alaninals and L-serinals in the presence of Lewis acids. Total synthesis of cis-(2R,3S)-3-hydroxyproline

The influence of Lewis acids on the diastereoselectivity of the addition of allyltrimethylsilane to variously protected L-alaninals and L-serinals was investigated and high levels of asymmetric induction were achieved. Stereochemical models for rationalisation of the results obtained are proposed. cis-(2R,3S)-3-Hydroxyproline was synthesised starting from N-Cbz, O-TBS-L-serinal, in which the crucial step involves addition of allyltrimethylsilane to the aldehyde in the presence of SnCl4.