461385-12-6

Basic information

• Product Name: 2R,2'R,5R,6S-2-(2'-((benzyl)(benzyloxycarbonyl)amino)-4'-oxobutyl)-5,6-diphenylmorpholine-4-carboxylic acid benzyl ester
• Synonyms: 2R,2'R,5R,6S-2-(2'-((benzyl)(benzyloxycarbonyl)amino)-4'-oxobutyl)-5,6-diphenylmorpholine-4-carboxylic acid benzyl ester
• CAS NO: 461385-12-6
• Molecular Weight: 682.816
• Mol File: 461385-12-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2R,2'R,5R,6S-2-(2'-((benzyl)(benzyloxycarbonyl)amino)-4'-oxobutyl)-5,6-diphenylmorpholine-4-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2R,2'R,5R,6S-2-(2'-((benzyl)(benzyloxycarbonyl)amino)-4'-oxobutyl)-5,6-diphenylmorpholine-4-carboxylic acid benzyl ester(461385-12-6)
• EPA Substance Registry System: 2R,2'R,5R,6S-2-(2'-((benzyl)(benzyloxycarbonyl)amino)-4'-oxobutyl)-5,6-diphenylmorpholine-4-carboxylic acid benzyl ester(461385-12-6)

Safety Data

• Hazardous Substances Data: 461385-12-6(Hazardous Substances Data)

Upstream product

• 461385-07-9 2R,5R,6S-2-(methoxycarbonylmethyl)-5,6-diphenylmorpholine-4-carboxylic acid benzyl ester 
• 461385-08-0 2R,5R,6S-2-(2-oxoethyl)-5,6-diphenylmorpholine-4-carboxylic acid benzyl ester 
• 501-53-1 benzyl chloroformate 
• 461385-09-1 2R,5R,6S-2-(2-(benzylimino)ethyl)-5,6-diphenylmorpholine-4-carboxylic acid benzyl ester 

Downstream Products

• 461385-13-7 2R,2'R,5R,6S-2-(2'-((benzyl)(benzyloxycarbonyl)amino)-3'-carboxypropyl)-5,6-diphenylmorpholine-4-carboxylic acid benzyl ester 
• 461385-14-8 (2S,3R,6R)-6-[(R)-2-(Benzyl-benzyloxycarbonyl-amino)-3-(N'-benzyloxycarbonylmethyl-N'-methyl-hydrazinocarbonyl)-propyl]-2,3-diphenyl-morpholine-4-carboxylic acid benzyl ester 
• 33404-78-3 negamycin 

Relevant articles and documents

Asymmetric synthesis of (+)-negamycin

An asymmetric synthesis of the antibiotic (+)-negamycin (1) has been achieved, starting from commercially available (5R,6S)-4-(benzyloxycarbonyl)- 5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (2). The synthesis involved the stabilized Wittig olefination of the lactone carbonyl group of 2 and subsequent asymmetric hydrogenation to generate the corresponding all-syn oxazine 4 with excellent diastereoselectivity. Conversion of 4 into β-alkoxy imine 7 and subsequent CeCl3-promoted chelation-controlled allylation of 7 generated the corresponding homoallylamine 8 with good diatereoselectivity, which was readily converted into (+)-negamycin (1) in 25% overall yield over 11 steps.