221676-92-2

Basic information

• Product Name: (2S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-(methoxycarbonyl)methyl-1-(phenylsulfonyl)pyrrolidine isopropylidine ketal
• Synonyms: (2S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-(methoxycarbonyl)methyl-1-(phenylsulfonyl)pyrrolidine isopropylidine ketal
• CAS NO: 221676-92-2
• Molecular Weight: 369.439
• Mol File: 221676-92-2.mol

Chemical Properties

• CAS DataBase Reference: (2S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-(methoxycarbonyl)methyl-1-(phenylsulfonyl)pyrrolidine isopropylidine ketal(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-(methoxycarbonyl)methyl-1-(phenylsulfonyl)pyrrolidine isopropylidine ketal(221676-92-2)
• EPA Substance Registry System: (2S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-(methoxycarbonyl)methyl-1-(phenylsulfonyl)pyrrolidine isopropylidine ketal(221676-92-2)

Safety Data

• Hazardous Substances Data: 221676-92-2(Hazardous Substances Data)

Upstream product

• 5927-18-4 trimethyl phosphonoacetate 
• 119593-29-2 (4aS,7aS)-5-Benzenesulfonyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-6-ol 

Downstream Products

• 221676-97-7 methyl (2S,4S,5S)-4-tert-butyldimethylsilyloxy-5-tert-butyldimethylsilyloxy-methyl-1-phenylsulfonylpyrrolidine-2-acetate 
• 221677-05-0 (2R,3S,5S)-3-tert-butyldimethylsilyloxy-1-benzyloxycarbonyl-5-β-hydroxyethylproline tert-butyl ester 
• 221677-06-1 (2R,3S,5S)-3-tert-butyldimethylsilyloxy-1-benzyloxycarbonyl-5-β-bromoethylproline tert-butyl ester 
• 221676-99-9 (2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-methoxycarbonylmethyl-1-phenylsulfonylproline tert-butyl ester 
• 221677-00-5 (2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-β-hydroxyethyl-1-phenylsulfonylproline tert-butyl ester 
• 221677-01-6 (2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-β-bromoethyl-1-phenylsulfonylproline tert-butyl ester 
• 221676-98-8 methyl (2S,4S,5S)-4-tert-butyldimethylsilyloxy-5-hydroxymethyl-1-phenylsulfonylpyrrolidine-2-acetate 
• 221677-02-7 (2R,3S,5S)-5-β-bromoethyl-3-hydroxy-1-phenylsulfonylproline tert-butyl ester 
• 221676-96-6 methyl (2S,4S,5S)-4-hydroxy-5-hydroxymethyl-1-phenylsulfonylpyrrolidine-2-acetate 

Relevant articles and documents

Conformationally constrained 7-azabicyclo[2.2.1]heptane amino acids. Synthesis of a glutamic acid analogue

We report the synthesis of 2-substituted 7-azabicyclo[2.2.1]heptane glutamic acid analogue 27 from L-serine. Hemiaminal intermediate 2 can be converted to the 2S,3S,5S-trisubstituted pyrrolidine 3 by a tandem Wittig/Michael reaction or to the 2S,3S,5R-trisubstituted pyrrolidine 4 via an iodosulfonamidation reaction. The key transannular alkylation step to form the [2.2.1] ring system involves a β-elimination of a silyl ether followed by cyclization to afford tert-butyl 7-benzyloxycarbonyl-7-azabicyclo[2.2.1]- 2-heptene-1-carboxylate (20). Selective functionalization at C-2 was accomplished by the direct reduction with SmI2 of 2-keto-3-silyl ether 23 to the C-2 ketone 24, which was converted to α,β-unsaturated ester 25. Stereospecific reduction of the double bond from the exo face leads to a single protected glutamate analogue, tert-butyl (1S,2R,4R)-7- benzyloxycarbonyl-2-(methoxycarbonylmethyl)-7-azabicyclo[2.2.1]heptane-1- carboxylate (27).