916154-05-7

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 824-94-2 p-methoxybenzyl chloride 
• 111830-53-6 1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose 
• 913258-74-9 3,6-O-di-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-D-glucal 
• 916154-04-6 ((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol 

Downstream Products

• 947305-46-6 (2R,3S,4R)-3-(4-methoxybenzyloxy)-2-vinyl-3,4-dihydro-2H-pyran-4-ol 
• 1163128-49-1 (1S,5R,6R)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-3-cyclohexene-1-carbaldehyde 
• 916154-11-5 (S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-(p-methoxybenzyloxy)hept-6-enoate 
• 916154-08-0 (S)-hept-6-en-2-yl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate 
• 916154-09-1 (S)-hept-6-en-2-yl (3R,4S,5S)-5-benzyloxy-3-hydroxy-4-(p-methoxybenzyloxy)hept-6-enoate 
• 916154-07-9 methyl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate 
• 916154-12-6 (S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-hydroxyhept-6-enoate 

Relevant academic research and scientific papers

An Orthogonally Protected Cyclitol for the Construction of Nigerose- And Dextran-Mimetic Cyclophellitols

Cyclophellitols are potent inhibitors of exo- and endoglycosidases. Efficient synthetic methodologies are needed to fully capitalize on this intriguing class of mechanism-based enzyme deactivators. We report the synthesis of an orthogonally protected cycl

Sugar-based synthesis of tamiflu and its inhibitory effects on cell secretion

Tamiflu is currently the most effective drug for the treatment of influenza, but the insufficient supply and side-effects of this drug demand urgent solutions. We present a practical synthesis of Tamiflu by using novel synthetic routes, cheap reagents, and the abundantly available starting material D-glucal. The strategy features a Claisen rearrangement of hexose to obtain the cyclohexene backbone and introduction of diamino groups through tandem intramolecular aziridination and ring opening. In addition, this synthetic protocol allows late-stage functionalization for the flexible synthesis of Tamiflu analogues. By using the synthesized Tamiflu and its active metabolite (oseltamivir carboxylate), we inves-tigated their influences on neuroendocrine PC12 cells in various aspects. It was discovered that oseltamivir carboxylate significantly inhibits the vesicular exocytosis (regulated secretion) of PC 12 cells, and suggests a mechanism underlying the Tamiflu side-effects, in particular its possible adverse influences on neurotransmitter release in the central nervous system.

METHOD OF FORMING OSELTAMIVIR AND DERIVATIVES THEREOF

A process is provided for the synthesis of 4,5-diamino cyclohexene carboxylate ester (1): or a pharmaceutically acceptable salt thereof. R1 - R3 are a silyl-, an aliphatic, alicyclic, aromatic, arylaliphatic, or an arylalicyclic group. R4, R11 and R12 are H, a silyl-group, an aliphatic, alicyclic, aromatic, arylaliphatic, or an arylalicyclic group. 3,4-Dihydropyran compound (9): with R5 and R6 being suitable protecting groups, is reacted to form aldehyde (4): which is oxidized and converted to N-substituted carbamate (3): with R7 being a suitable protecting group. (3) is, via oxazolinidone (13): converted to azido carboxylate ester (2): and then to 4,5-diamino cyclohexene carboxylate ester (1).

The first total synthesis of sporiolide A

The first total synthesis of the natural cytotoxic agent sporiolide A has been accomplished from D-glucal in 16 steps with 6.1% overall yield. Carbohydrates were applied as the chiral templates to manipulate the absolute configuration during the synthesis