132249-34-4

Upstream product

• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 21149-17-7 methyl 2-(benzyloxycarbonylamino)acrylate 
• 153277-33-9 N-benzyloxycarbonyl-S-phenyl-L-cysteine methyl ester 
• 3693-94-5 C₁₄H₁₇NO₅S 
• 1259419-30-1 methyl N-(benzyloxycarbonyl)-Se-phenyl-L-selenocysteinate 
• 82611-65-2 N-benzyloxycarbonyl-S-phenyl-L-cysteine 
• 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 
• 153277-22-6 (R)-benzyl (1-hydroxy-3-(phenylthio)propan-2-yl)carbamate 
• 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 
• 153277-28-2 (2S,3S,3'S)-2-<4'-(tert-Butyldimethylsilyloxy)-3'-(benzyloxycarbonylamino)butyl>-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine 
• 153277-32-8 (2S,3S)-2-((S)-3-Benzyloxycarbonylamino-4-methanesulfonyloxy-butyl)-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 153277-31-7 (2S,3S)-2-((S)-3-Benzyloxycarbonylamino-4-hydroxy-butyl)-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 153277-21-5 (R)-2-Benzyloxycarbonylamino-1-(tert-butyldimethylsilyloxy)-3-phenylsulfonylpropane 
• 153277-34-0 (R)-2-Benzyloxycarbonylamino-1-(tert-butyldimethylsilyloxy)-3-phenylthiopropane 
• 153379-66-9 (1S,6S,8aS)-6-(benzyloxycarbonylamino)octahydroindolizin-1-yl acetate 

Relevant academic research and scientific papers

Straightforward method for the synthesis of selenocysteine and selenocystine derivatives from L-serine methyl ester

A set of selenoamino acids has been efficiently synthesized under smooth conditions by a simple, flexible and modular strategy. In this method, O-mesylated l-serine methyl ester is generated in situ and directly substituted with various selenolate anions

A novel method for the synthesis of thioacetates using benzyltriethyl- ammonium tetrathiomolybdate and acetic anhydride

Herein we report a simple and efficient methodology for the synthesis of thioacetates using benzyltriethylammonium tetrathiomolybdate and acetic anhydride as the key reagents, starting from alkyl halides in a multistep, tandem reaction process. Its application in the synthesis of orthogonally protected cysteine and anomeric β-thioglycosides has also been demonstrated.

A short synthetic approach to chiral serine azido derivatives

We report a new synthetic methodology for the synthesis of chiral serine azido derivatives through a conversion of N-protected (Boc, Cbz and Fmoc) serine amino acid into its corresponding Weinreb amide. Thus, acidity of the α-proton of the serine is reduced and it allows nucleophilic addition reaction onto Weinreb amide to furnish chiral serine azido derivatives.

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.

A total synthesis of (-)-slaframine from (+)-cis-(2R,3S)-3-hydroxyproline

A total synthesis of the naturally occurring indolizidine (-)-Slaframine 4 has been achieved, starting from the cis-3-hydroxyproline derivative 1, in which a key step is a Julia olefination reaction using the dianion derived from the β-aminosulfone 5.