135582-87-5

Basic information

• Product Name: (S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxypropanoate
• Synonyms: (S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxypropanoate
• CAS NO: 135582-87-5
• Molecular Weight: 253.255
• Mol File: 135582-87-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxypropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxypropanoate(135582-87-5)
• EPA Substance Registry System: (S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxypropanoate(135582-87-5)

Safety Data

• Hazardous Substances Data: 135582-87-5(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 42491-79-2 (2S)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxypropanoic acid 
• 91174-01-5 sodium [(benzyloxy)carbonyl]chloroamide 
• 292638-85-8 acrylic acid methyl ester 
• 621-84-1 O-benzyl carbamate 
• 501-53-1 benzyl chloroformate 
• 67-56-1 methanol 
• 385836-99-7 (S)-(2,2-dimethyl-5-oxo-[1,3]dioxalan-4-ylmethyl)carbamic acid benzyl ester 

Downstream Products

• 1429470-98-3 benzyl (5R)-2,2-dimethyl-5-[(1E)-3-oxobut-1-en-1-yl]-1,3-oxazolidine-3-carboxylate 
• 1429470-99-4 benzyl (5R)-2,2-dimethyl-5-[(1Z)-3-oxobut-1-en-1-yl]-1,3-oxazolidine-3-carboxylate 
• 134038-73-6 benzyl (S)-5-hydroxymethyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 1429471-04-4 benzyl (5S)-5-[(1R,2R)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 1429471-03-3 benzyl (5S)-5-[(1S,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 1429470-96-1 benzyl (5S)-5-[(1S,2R)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 1429470-97-2 benzyl (5S)-5-[(1R,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 

Relevant articles and documents

Structural Insights Lead to a Negamycin Analogue with Improved Antimicrobial Activity against Gram-Negative Pathogens

Negamycin is a natural product with antibacterial activity against a broad range of Gram-negative pathogens. Recent revelation of its ribosomal binding site and mode of inhibition has reinvigorated efforts to identify improved analogues with clinical potential. Translation-inhibitory potency and antimicrobial activity upon modification of different moieties of negamycin were in line with its observed ribosomal binding conformation, reaffirming stringent structural requirements for activity. However, substitutions on the N6 amine were tolerated and led to N6-(3-aminopropyl)-negamycin (31f), an analogue showing 4-fold improvement in antibacterial activity against key bacterial pathogens. This represents the most potent negamycin derivative to date and may be a stepping stone toward clinical development of this novel antibacterial class.

Short synthesis of (+)-1-deoxynojirimycin via a diastereoselective reductive coupling of alkyne and -chiral aldehyde

A short, highly diastereoselective synthesis of (+)-1-deoxynojirimycin from readily available l-isoserine with overall yield of 32.0% in eight steps is described. The key step includes a diastereoselective syn-coupling reaction of Cbz-protected (S)-iso-serinal acetonide 6 and vinylzinc nucleophile, generated conveniently from a protected propargyl alcohol 7 by a hydrozirconation- transmetalation sequence. Significantly, not only does this simple flexible strategy provide a concise approach to (+)-1-deoxynojirimycin, but it also can readily be adopted for the synthesis of other stereoisomers of the 1-deoxynojirimycin family from l- or d-iso-serine through different coupling conditions and stereoselective -epoxidation of allylic alcohol 4 by the same procedures. Georg Thieme Verlag Stuttgart · New York.

Erhoehung der Effizienz der katalytischen asymmetrischen Aminohydroxylierung durch N-Halogencarbamat-Salze

Keywords: Aminoalkohole; Asymmetrische Aminohydroxylierung; Carbamate; Katalyse