81176-31-0

Upstream product

• 98-88-4 benzoyl chloride 
• 81069-01-4 N-[(S)-1-((1S,2S)-1,2-Dihydroxy-propyl)-but-3-enyl]-benzamide 
• 82266-95-3 (+)-lyxo-3-(Benzoylamino)-2,3,6-trideoxyhexanoic acid γ-lactone 
• 104465-69-2 3-(benzoylamino)-4,5-O-bis(methoxymethyl)-2,3,6-trideoxy-L-lyxo-hexose diethyl dithioacetal 
• 104465-68-1 3-(benzoylamino)-2,3,6-trideoxy-4,5-O-bis(methoxymethyl)-L-lyxo-hexose ethylene acetal 
• 75712-53-7 (3S,4S,5S)-3-benzamido-4-hydroxy-5-hexanolide 
• 99630-06-5 t-butyl (4S,5S,2Z)-3-amino-4,5-(cyclohexylidenedioxy)-2-hexenoate 
• 90819-77-5 t-butyl (3S,4S,5S)-3-acetamido-4,5-(cyclohexylidenedioxy)hexanoate 
• 90865-23-9 t-butyl (4S,5S,2Z)-3-acetamido-4,5-(cyclohexylidenedioxy)-2-hexenoate 
• 109170-88-9 (4S,5S)-5-Carbamoyloxy-4-hydroxy-hex-2-ynoic acid methyl ester 
• 104545-83-7 (S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-hex-2-ynoic acid methyl ester 
• 109360-98-7 (4S,5S)-5-Hydroxy-4-(tetrahydro-pyran-2-yloxy)-hex-2-ynoic acid methyl ester 
• 104572-12-5 (Z)-(4S,5S)-5-Carbamoyloxy-4-triethylsilanyloxy-hex-2-enoic acid methyl ester 
• 109170-89-0 (4S,5S)-5-Carbamoyloxy-4-triethylsilanyloxy-hex-2-ynoic acid methyl ester 

Relevant academic research and scientific papers

A STEREOSELECTIVE SYNTHESIS OF N-BENZOYL L-DAUNOSAMINE

Reaction of (2S,3S)-2,3-(cyclohexylidenedioxy)butanenitrile, derived from L(+)-tartrate or (S)-lactate, with the magnesium enolate of t-butyl acetate gave the corresponding (Z)-β-amino acrylate derivative, which was in turn transformed into N-benzoyl L-da

A new route to 3-amino sugars. A concise synthesis of L-daunosamine and D-ristosamine derivatives

An asymmetric aldol strategy has been developed for the synthesis of L- daunosamine and D-ristosamine derivatives starting from noncarbohydrate precursors. Lithium and boron enolate mediated aldol reactions of 12 with O- TBS lactaldehyde gave non-Evans syn and Evans syn aldol products, respectively, with high selectivity. The chemical efficiency of the lithium enolate reactions were higher than the corresponding reactions with the boron enolates. Curtius rearrangement of lactone acids 23 and 26 gave the corresponding N-BOC amino lactones 30 and 32 in 64% and 62%, respectively, with complete retention of configuration. Lactone 30 was converted by a two- step sequence to N-benzoyldaunosamide 40. The overall yield for the amino sugar 40 was 18% over six steps. Similary, lactone 32 was converted to N- benzoylristosamide 42 with an overall yield of 18% starting from 12.

Total syntheses of N-trifluoroacetyl-L-daunosamine, N-trifluoroacetyl-L-acosamine, N-benzoyl-D-acosamine, and N-benzoyl-D-ristosamine from an achiral precursor, methyl sorbate

A conjugated addition of benzylamine to methyl (4R,5S)-4,5-(isopropylidenedioxy)-(2E)-hexenoate (12) followed by lactonization under acidic condition proceeds formally to the total syntheses of L-daunasamine (1) and L-acosamine (2). On the other hand, direct conjugated addition of benzylamine to methyl (4S,5S)-4,5-epoxy-(2E)-hexenoate (4) and the subsequent intramolecular nucleophilic attack by ester carbonyl group against epoxy ring of the substrates leads to the formal total syntheses of D-acosamine (2) and D-ristosamine (3).

Stereoselective Synthesis of 3-Amino 1,2-Diols via Intermolecular Pinacol Cross-Coupling of α-Aldehydes with Aliphatic Aldehydes. Short Asymmetric Syntheses of Two 2,3,6-Trideoxy-3-amino Sugars

syn,syn-3-Amino 1,2-diols are prepared via a pinacol cross coupling reaction between N-Cbz- or N-Boc-α-amino aldehydes and aliphatic aldehydes.Application of this methodology to the synthesis of two amino sugars starting from N-Cbz-L-aspartic acid are described.

Stereochemistry of the Epoxidations of Acyclic Allylic Amides. Applications toward the Synthesis of 2,3,6-Trideoxy-3-aminohexoses

The stereochemistry of the epoxidation of several acyclic allylic amides is described.Diastereoselectivity in the (Z)-allylic amide series (compound 1) proved to be dependent both on the amide functionality and epoxidation reagent.The threo epoxide 3 was

THE CHEMISTRY OF SILYLATED KETENE ACETALS: AN EFFICIENT STEREOCONTROLLED SYNTHESIS OF N-BENZOYL L-DAUNOSAMINE

N-Benzoyl L-daunosamine was synthesized with high stereoselectivity utilizing a 1,3-addition of ketene silyl acetal (3a) to the chiral nitrone, (Z)-((4R)-trans-2,2,5-trimethyl-1,3-dioxolan-4-yl)methylene((1S)-1-phenylethyl)amine N-oxide (4c) accompanied by a silyl group-transfer in acetonitrile under mild conditions.

A New Synthesis of 3-Amino-2-alkenoates. Novel Synthetic Route to Amino Sugars N-benzoyl-L-daunosamine and -L-acosamine

Alkanoate esters are found to couple with various nitriles to give (Z)-3-amino-2-alkenoates in good yields with the aid of a magnesium amide prepared by the reaction of ethylmagnesium bromide and diisopropylamine.The C-C bond forming reaction was applied

New Acyclic Approach to 3-Amino-2,3,6-trideoxy-L-hexoses: a Stereocontrolled Synthesis of N-Benzoyl L-Daunosamine

N-Benzoyl L-daunosamine was synthesized stereoselectively starting from O-t-butyldimethylsilyl L-lactaldehyde and methyl propiolate; the crucial step, intramolecular conjugate addition of a carbamoyl amino group of methyl threo-5-carbamoyloxy-4-triethylsi

DIASTEREOSELECTIVE SYNTHESIS OF N-ACETYL-D,L-ACOSAMINE AND N-BENZOYL-D,L-RISTOSAMINE

N-Acyl derivatives of D,L-acosamine and D,L-ristosamine were synthesized with high stereoselectivity utilizing intramolecular Michael addition of γ- and δ-carbamoyloxy-α,β-unsaturated esters.