119874-56-5

Upstream product

• 119943-96-3 Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside 
• 80667-89-6 (4aR,6S,8R,8aS)-8-(benzyloxy)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine 
• 6752-48-3 (4aR,6S,8R,8aS)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-ol 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 79241-07-9 (R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan 
• 100-39-0 benzyl bromide 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 6752-48-3 methyl 4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 65556-00-5 methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside 
• 68144-11-6 1,4-anhydro-2-deoxy-5,6-O-isopropylidene-D-arabinohex-1-enitol 
• 6160-67-4 (D)-mannose diacetonide 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 93714-01-3 methyl 3-O-benzyl-α-D-mannopyranoside 
• 13145-22-7 methyl 2-deoxy-α-D-glucopyranoside 

Downstream Products

• 389065-68-3 (2R,4R,6S)-4-Benzyloxy-6-methoxy-2-methyl-dihydro-pyran-3-one 
• 90762-83-7 Methyl 3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside 
• 107908-97-4 methyl 2,6-dideoxy-3-O-benzyl-α-D-lyxo-hexopyranoside 
• 913639-36-8 methyl 3-O-benzyl-2,4-dideoxy-α-pent-4-enopyranoside 
• 614752-28-2 (2S,4S,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran 
• 87391-88-6 [(2S,4S,6S)-4-(benzyloxy)-6-methoxytetrahydro-pyran-2-yl]-methanol 
• 68711-40-0 (3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone 
• 104872-04-0 Orlistat 
• 925684-05-5 methyl (3S,5R)-3-(benzyloxy)-5-(methoxymethoxy)hexadecanoate 
• 925684-04-4 (4S,6R)-4-(benzyloxy)-6-undecyltetrahydro-2H-pyran-2-one 
• 925684-02-2 (2S,4S,6R)-4-(benzyloxy)-6-undecyltetrahydro-2H-pyran-2-ol 
• 925684-01-1 (2S,4S,6R)-4-(benzyloxy)-2-methoxy-6-undecyltetrahydro-2H-pyran 
• 925683-99-4 (2S,4S,6S)-4-(benzyloxy)-2-methoxy-6-(tosyloxymethyl)tetrahydro-2H-pyran 
• 925683-97-2 (2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxy-3-{[(methylsulfanyl)carbothioyl]oxy}tetrahydro-2H-pyran 

Relevant academic research and scientific papers

Stereoselective epoxidation of 4-deoxypentenosides: A polarized-π model

The high facioselectivity in the epoxidation of 4-deoxypentenosides (4-DPs) by dimethyldioxirane (DMDO) correlates with a stereoelectronic bias in the 4-DPs' ground-state conformations, as elucidated by polarized-π frontier molecular orbital (PPFMO) analy

Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides

Glycals and 4-deoxypentenosides (4-DPs), unsaturated pyranosides with similar structures and reactivity profiles, can exhibit a high degree of stereoselectivity upon epoxidation with dimethyldioxirane (DMDO). In most cases, the glycals and their corresponding 4-DP isosteres share the same facioselectivity, implying that the pyran substituents are largely responsible for the stereodirecting effect. Fully substituted dihydropyrans are subject to a "majority rule", in which the epoxidation is directed toward the face opposite to two of the three groups. Removing one of the substituents has a variable effect on the epoxidation outcome, depending on its position and also on the relative stereochemistry of the remaining two groups. Overall, we observe that the greatest loss in facioselectivity for glycals and 4-DPs is caused by removal of the C3 oxygen, followed by the C5/anomeric substituent, and least of all by the C4/C2 oxygen. DFT calculations based on polarized-π frontier molecular orbital (PPFMO) theory support a stereoelectronic role for the oxygen substituents in 4-DP facioselectivity, but less clearly so in the case of glycals. We conclude that the anomeric oxygen in 4-DPs contributes toward a stereoelectronic bias in facioselectivity whereas the C5 alkoxymethyl in glycals imparts a steric bias, which at times can compete with the stereodirecting effects from the other oxygen substituents.

A chiron approach to (-)-tetrahydrolipstatin

An efficient chiron approach to the total synthesis of (-)- tetrahydrolipstatin is described. The main features of the synthetic strategy, which starts from tri-O-acetyl-D-glucal, are copper-mediated C-C bond formation, Frater alkylation, and Barton-McCombie deoxygenation. Georg Thieme Verlag Stuttgart.

Novel γ-secretase inhibitors discovered by library screening of in-house synthetic natural product intermediates

Screening of our in-house compound library comprised of intermediates of natural product synthesis projects resulted in discovering two novel γ-secretase inhibitors, which coincidently had similar moieties, that is, cyclohexenone and two aryl groups arran

Total synthesis of (+)-myriocin and (-)-sphingofungin E from aldohexoses using overman rearrangement as the key reaction

Total synthesis starting from aldohexoses of naturally occurring α-substituted α-amino acids, (+)-myriocin (1) and (-)-sphingofungin E (2), is described. Overman rearrangement of allylic trichloroacetimidate 6E derived from D-mannose effectively generated the tetrasubstituted carbon with nitrogen, and subsequent Wittig olefination afforded the highly functionalized moiety 3 of myriocin stereoselectively. Sulfone-mediated coupling reaction of the allyl bromide 3 with C12 hydrophobic part 4 successfully constructed the carbon framework possessing E-olefin 28. Removal of the sulfone and protecting groups completed the chiral and stereoselective total synthesis of (+)-myriocin (1). A similar transformation starting from D-glucose also accomplished the total synthesis of (-)-sphingofungin E (2).

Novel and convenient method for the syntheses of 2,6-dideoxypyranoses, 3,6-dideoxypyranoses, and azido (amino) analogs of 3,6-dideoxypyranoses

A novel method of regioselective deoxygenation of methyl 4,6-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside, and its application for the syntheses of 2,6-dideoxypyranoses, 3,6-dideoxypyranoses, and azido (amino) analogs of 3,6-dideoxypyranoses were reported.