135905-09-8

Basic information

• Product Name: (2R,3R)-2-[(R)-3-Methanesulfonyloxy-1-(2-trimethylsilanyl-ethoxymethoxymethyl)-propyl]-3-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolidine-1-carboxylic acid benzyl ester
• Synonyms: (2R,3R)-2-[(R)-3-Methanesulfonyloxy-1-(2-trimethylsilanyl-ethoxymethoxymethyl)-propyl]-3-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolidine-1-carboxylic acid benzyl ester
• CAS NO: 135905-09-8
• Molecular Weight: 647.978
• Mol File: 135905-09-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,3R)-2-[(R)-3-Methanesulfonyloxy-1-(2-trimethylsilanyl-ethoxymethoxymethyl)-propyl]-3-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolidine-1-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-2-[(R)-3-Methanesulfonyloxy-1-(2-trimethylsilanyl-ethoxymethoxymethyl)-propyl]-3-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolidine-1-carboxylic acid benzyl ester(135905-09-8)
• EPA Substance Registry System: (2R,3R)-2-[(R)-3-Methanesulfonyloxy-1-(2-trimethylsilanyl-ethoxymethoxymethyl)-propyl]-3-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolidine-1-carboxylic acid benzyl ester(135905-09-8)

Safety Data

• Hazardous Substances Data: 135905-09-8(Hazardous Substances Data)

Upstream product

• 501-53-1 benzyl chloroformate 
• 95456-65-8 (3aR,6aR)-2-Oxo-hexahydro-furo[3,2-b]pyrrole-4-carboxylic acid benzyl ester 
• 135905-08-7 (2SR,3SR,1'SR)-1-(Benzyloxycarbonyl)-3-<2-(trimethylsilyl)ethoxymethoxy>-2-<<2-(trimethylsilyl)ethoxymethoxymethyl>but-3'-en-1'-yl>pyrrolidine 
• 135904-95-9 (1SR,4SR,5SR)-6-(Benzyloxycarbonyl)-4-(prop-2-en-1-yl)-2-oxa-6-azabicyclo<3.3.0>octan-3-one 
• 135904-96-0 (2SR,3SR,βSR)-1-(Benzyloxycarbonyl)-3-hydroxy-β-(prop-2-en-1-yl)pyrrolidine-2-ethanol 
• 76513-69-4 (2-trimethylethylsilylethoxy)methyl chloride 
• 135905-10-1 (2SR,3SR,γSR)-1-(Benzyloxycarbonyl)-3-<2-(trimethylsilyl)ethoxymethoxy>-γ-<2-(trimethylsilyl)ethoxymethoxymethyl>pyrrolidine-2-propanol 
• 124-63-0 methanesulfonyl chloride 

Relevant articles and documents

Homoproline homologation by enolate Claisen rearrangement or direct allylation: Syntheses of (-)-trachelanthamidine, (-)-isoretronecanol and (±)-turneforcidine

The pyrrolizidine precursors 13 and 14 are obtained both by enolate Clalsen rearrangement of the homoproline allyl ester 12 and by direct allylation of N-protected homoproline ethyl ester 15. In both cases, the reactions show poor levels of stereoselectivity. Reduction gives the corresponding alcohols 20a and 21 a which are separated and subsequently elaborated to (-)-trachelanthamidine 24 and (-)-isoretronecanol 25 respectively via reductive alkene cleavage, mesylation and spontaneous cyclisation following N-deprotection. The chiral integrity of the original proline-derived asymmetric centre is preserved throughout. A similar enolate allylation gives, with high stereoselectivity, the homologue 34 of the Geissman-Waiss lactone 32, which is similarly transformed into (±)-turneforcidine 31.