81176-33-2

Upstream product

• 98-88-4 benzoyl chloride 
• 1730-25-2 allylmagnesium bromide 
• 128414-13-1 ((1S,2R,3R)-1-[1,3]Dithiolan-2-ylmethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester 
• 128414-15-3 [(2R,3S)-2-((R)-1-Hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-yl]-carbamic acid benzyl ester 
• 192824-03-6 {(2S,3S)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-oxo-tetrahydro-furan-3-yl}-carbamic acid tert-butyl ester 
• 192824-01-4 (2S,3S)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-oxo-tetrahydro-furan-3-carboxylic acid 
• 192824-05-8 (3S,4S,5R)-3-(N-tert-butoxycarbonylamino)-5-dihydroxy-4-hexanolactone 
• 194229-42-0 methyl (3S,4S,5S)-3-benzylamino-4,5-epoxyhexanoate 
• 194229-45-3 (3S,4S,5R)-ribo-3-benzylamino-trideoxyaldonic acid γ-lactone 
• 67315-16-6 methyl (4S,5S)-(4,5)-epoxy-2(E)-hexenoate 
• 100484-30-8 (3S,4S,5R)-3-benzamido-5-hydroxy-4-hexanolide 
• 58769-79-2 N-((2R,3S,4S,6S)-3-Hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-4-yl)-benzamide 
• 62812-43-5 N-((2R,3S,4S,6R)-3-Hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-4-yl)-benzamide 
• 102147-63-7 ((4R,5R,6S)-6-Methyl-2-oxo-5-triethylsilanyloxy-[1,3]oxazinan-4-yl)-acetic acid ethyl ester 

Relevant academic research and scientific papers

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).

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.

TARTRALDEHYDES III. SYNTHESIS OF N-BENZOYL-L-RISTOSAMINE AND -L-ACOSAMINE

The title compounds have been synthesized from the (2R,3S)-tartraldehyde mercaptal 4 in seven steps with 21percent overall yield.

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.

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

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

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.

Total Synthesis of Optically Active N-Benzoyldaunosamine from an Azetidinone

The azetidinone adduct 5 formed from chlorosulfonyl isocyanate and (E)-1,3-pentadiene was employed as a key intermediate to accomplish an efficient synthesis of optically active LS-N-benzoyldaunosamine (1b).

Stereospecific Synthesis of N-Benzoyl-L-daunosamine and L-Ristosamine

The synthesis of N-Benzoyl-L-daunosamine (7) and L-ristosamine (8) from the C4 2R,3S and 2S,3S aldehydes 1 and 3 through the intermediacy of the C7-N adducts 5 and 6, formed by erythro addition of diallylzinc onto the phenylsulfenimines 2 and 4, is reported.