864360-81-6

Basic information

• Product Name: [N-tert-butoxycarbonyl-[2-(dimethylphenylsilanyl)-but-2-enyl]-amino]-acetic acid [1S,5R]-2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-3-yl)-ethyl ester
• Synonyms: [N-tert-butoxycarbonyl-[2-(dimethylphenylsilanyl)-but-2-enyl]-amino]-acetic acid [1S,5R]-2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-3-yl)-ethyl ester
• CAS NO: 864360-81-6
• Molecular Weight: 511.777
• Mol File: 864360-81-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [N-tert-butoxycarbonyl-[2-(dimethylphenylsilanyl)-but-2-enyl]-amino]-acetic acid [1S,5R]-2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-3-yl)-ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [N-tert-butoxycarbonyl-[2-(dimethylphenylsilanyl)-but-2-enyl]-amino]-acetic acid [1S,5R]-2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-3-yl)-ethyl ester(864360-81-6)
• EPA Substance Registry System: [N-tert-butoxycarbonyl-[2-(dimethylphenylsilanyl)-but-2-enyl]-amino]-acetic acid [1S,5R]-2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-3-yl)-ethyl ester(864360-81-6)

Safety Data

• Hazardous Substances Data: 864360-81-6(Hazardous Substances Data)

Upstream product

• 35836-73-8 (-)-nopol 
• 320618-85-7 [N-tert-butoxycarbonyl-N-(2-phenyldimethylsilylbut-2(Z)-enyl)amino]acetic acid 
• 320618-86-8 N-tert-butoxycarbonyl-N-[2-(dimethylphenylsilanyl)but-2(Z)-enyl]glycine methyl ester 
• 320618-66-4 1-bromo-2-(dimethylphenylsilanyl)but-2(E)-ene 
• 31954-27-5 N-(tert-butoxycarbonyl)glycine methyl ester 

Relevant articles and documents

Asymmetric aza-[2,3]-Wittig sigmatropic rearrangements: Chiral auxiliary control and formal asymmetric synthesis of (2S, 3R, 4R)-4-hydroxy-3- methylproline and (-)-kainic acid

A survey of 16 different chiral auxiliaries and a variety of strategies found that an (-)-8-phenylmenthol ester of a glycine derived migrating group can control the absolute stereochemistry of aza-[2,3]-Wittig sigmatropic rearrangements with diastereoselectivities of ca. 3 : 1 with respect to the auxiliary. In two specific examples, ca. 50% yields of enantiomerically pure products were obtained after chromatographic purification. These were synthetically manipulated with no erosion of stereochemistry into intermediates that completed formal asymmetric syntheses of (+)-HyMePro and (-)-kainic acid. The Royal Society of Chemisrry 2005.