83532-10-9

Upstream product

• 501-53-1 benzyl chloroformate 
• 72075-74-2 methyl 3-azido-2,3,6-trideoxy-α-D-arabino-hexopyranoside 
• 18933-62-5 methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-α-D-arabino-hexopyranoside 
• 72062-88-5 Benzoic acid (2R,3R,4R,6S)-4-methanesulfonyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester 
• 18933-64-7 Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester 
• 6386-19-2 methyl 3-azido-4,6-O-benzylidene-2,3-dideoxy-α-D-arabino-hexopyranoside 
• 67693-33-8 methyl-3-amino-2,3,6-tridesoxy-α-D-arabino-hexopyranoside 
• 18944-96-2 methyl 4-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside 

Downstream Products

• 83532-11-0 methyl 3-(benzyloxycarbonyl)amino-2,3,6-trideoxy-α-arabino-hexopyranosid-4-ulose 
• 138456-69-6 methyl 3-(benzyloxycarbonyl)amino-4-(Z)-methoxymethylene-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside 
• 138456-68-5 methyl 3-(benzyloxycarbonyl)amino-4-(E)-methoxymethylene-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside 
• 138328-85-5 [(Z)-(R)-2-Formyl-1-(2-oxo-ethyl)-but-2-enyl]-carbamic acid benzyl ester 
• 75321-08-3 p-nitrobenzyl (5R,6S)-2-diphenoxy phosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate 
• 74288-39-4 (3S,4R)-3-[(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one 
• 75321-07-2 (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one 
• 78477-86-8 (3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(benzyloxycarbonyl)methyl>-2-azetidinone 
• 64067-13-6 p-nitrobenzyl (5R,6S)-2-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-2-em-3-carboxylate 
• 75363-99-4 4-nitrobenzyl (2R,5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 83532-14-3 {(2R,4R,6S)-6-Methoxy-3-[1-methoxy-meth-(Z)-ylidene]-2-methyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester 
• 83532-13-2 methyl 3-(benzyloxycarbonyl)amino-4-(diphenylphosphinoylmethoxy)methyl-2,3,6-trideoxy-α-D-arabino-hexopyranoside 
• 83532-15-4 methyl 3-(benzyloxycarbonyl)amino-4-methoxycarbonyl-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside 
• 83532-16-5 (3R,4S,5R)-3-(benzyloxycarbonyl)amino-4-methoxycarbonyl-5-hexanolide 

Relevant academic research and scientific papers

On the synthesis of aminoglycosides of cardioactive steroids: A study directed towards β-selective glycosylations of 3-aminodigitoxose with digitoxigenin analogues

Carbamate derivatives of 3-aminodigitoxose (D-ristosamine) were prepared, with the purpose of synthesizing 3-amino-β-digitoxosyl derivatives of cardioactive steroids. A 1,3 participation procedure, used under acid or mercury salt catalysis, and the imidate procedure were investigated. A careful fine tuning of the glycosylation conditions was necessary in order to obtain significant β-D-stereoselectivity, which proved to be mainly dependent on the polarity of the solvent and the relative reactivity of the sugar and the nucleophile.

Stereoselective reactions. XX. Synthetic studies on optically active β-lactams. III. Stereocontrolled synthesis of chiral intermediate to (+)-thienamycin from D-glucose

A chiral key intermediate (19a) for the synthesis of (+)-thienamycin was synthesized starting from D-glucose. The enol ether 13, obtained from the ketone 11 by Horner-Wittig reaction, was transformed to the corresponding methyl ester 16 by pyridinium chlorochromate oxidation or by employing the Wacker process. The ester 16 was further converted to the β-lactam 19a, which is a useful chiral precursor to (+)-thienamycin.