172603-41-7

Upstream product

• 93978-82-6 methyl 3-O-benzoyl-4-O-benzyl-2,6-dideoxy-β-L-lyxo-hexopyranoside 
• 93960-55-5 methyl 3-O-benzoyl-4-O-benzyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside 
• 93960-56-6 methyl 3-O-benzoyl-2,6-dideoxy-β-L-lyxo-hexopyranoside 
• 172603-37-1 methyl 2,6-dideoxy-3-O-(4-methoxybenzyl)-β-L-lyxo-hexopyranoside 
• 100-39-0 benzyl bromide 
• 62346-15-0 methyl 2,6-dideoxy-β-L-lyxo-hexopyranoside 
• 172603-39-3 methyl 4-O-benzyl-2,6-dideoxy-3-O-(4-methoxybenzyl)-β-L-lyxo-hexopyranoside 
• 83497-33-0 methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 

Downstream Products

• 93978-88-2 Methanesulfonic acid (2S,3R,4R,6S)-3-benzyloxy-4-cyano-6-methoxy-2-methyl-tetrahydro-pyran-4-yl ester 
• 93978-91-7 N-((2S,3S,4R,6S)-3-Benzyloxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-benzamide 
• 94062-88-1 (3S,4S,5S,7S)-4-Benzyloxy-7-methoxy-5-methyl-6-oxa-1-aza-spiro[2.5]octane 
• 75044-07-4 methyl 4-O-benzoyl-3-benzoylamino-2,3,6-trideoxy-3-C-methyl-α-L-xylo-hexopyranoside 
• 93978-85-9 methyl 4-O-benzyl-2,6-dideoxy-β-L-threo-hexopyranosid-3-ulose 

Relevant academic research and scientific papers

Stereoselective synthesis of L-vancosamine methyl β-glycoside by addition of an organocerium reagent to O-benzyloxime ethers

The methyl β-glycopyranoside of L-vancosamine (1, 3-amino-2,3,6-trideoxy-3-C-methyl-L-lyxo-hexose), a constituent of vancomycin and related glycopeptide antibiotics, was synthesized stereoselectivity from methyl 2,6-dideoxy-β-L-lyxo-hexopyranoside (2) in eight steps.Compound 2 was subjected in sequence to regioselective 3-O-p-methoxybenzylation, 4-O-tert-butyldimethylsilylation, oxidative 3-O-deprotection, and pyridinium dichromate oxidation to give methyl 4-O-tert-butyldimethylsilyl-2,6-dideoxy-β-L-threo-hexopyranosid-3-ulose (8).O-Benzyloximation of 8 and removal of the tert-butyldimethylsilyl protective group furnished methyl 2,6-dideoxy-β-L-threo-hexopyranosid-3-ulose O-benzyloxime (12).Addition of a methylcerium reagent to 12 provided the branched-chain hydroxyamino sugar methyl 3-benzyloxyamino-2,3,6-trideoxy-3-C-methyl-β-L-lyxo-hexopyranoside (14) which was easily converted into the title compound by hydrogenolysis.On the other hand, reaction of the 4-benzyl ether 11 with the organocerium reagent gave only traces of the 3-epi-analogue of 14, methyl 4-O-benzyl-3-benzyloxyamino-2,3,6-trideoxy-3-C-methyl-β-L-xylo-hexopyranoside.Keywords: Vancosamine; Branched-chain amino sugars; Organocerium reagents; Oxime ethers; Antibiotics

Branched-chain sugars. XXXVI. A new synthesis of methyl 4-O-benzoyl-3-benzoylamino-2,3,6-trideoxy-3-C-methyl-α-L-xylo-hexopyranoside, a derivative of the branched-chain amino sugar of antibiotic A35512B

The compound was synthesized from methyl 4-0-benzyl-2,6-dideoxy- beta -L-threo-hexopyranosid-3-ulose through cyanomesylation, reductive spiro aziridine formation, and reductive ring-opening. When (2-methyoxyethoxymethyl) group was used as the protecting g