50272-15-6

Upstream product

• 50272-14-5 methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-ribo-hexopyranoside 
• 40773-64-6 methyl 4,6-O-benzylidene-3-deoxy-ribo-hexopyranoside 
• 299199-12-5 methyl 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside 
• 214767-55-2 methyl 2-O-benzyl-3,6-dideoxy-6-iodo-α-D-ribo-hexopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 65530-28-1 methyl 4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 65556-00-5 methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside 
• 104652-29-1 2,2-Dimethyl-propionic acid (4aR,6S,7R,8S,8aS)-8-hydroxy-6-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 15354-29-7 methyl 4,6-O-isopropylidene-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 552890-29-6 2,2-Dimethyl-propionic acid (4aR,6S,7R,8aS)-6-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 552890-56-9 (4aR,6S,7R,8aS)-6-Methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 138665-01-7 Methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-ribo-hexopyranoside 

Downstream Products

• 178621-76-6 Acetic acid (2R,3S,5R,6S)-5-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 
• 552890-31-0 2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-6-methoxy-tetrahydro-pyran-3-yl ester 
• 1279711-62-4 methyl 2-O-benzyl-3-deoxy-5S-deutero-α-L-arabinopyranose 
• 1279711-49-7 methyl 2-O-benzyl-3,4-dideoxy-α-pent-4-enopyranoside 
• 1279711-76-0 C₁₃H₁₆O₄ 
• 178621-90-4 Benzoic acid (2R,3S,5R,6S)-2-[(2S,3R,4S,5R,6R)-6-((2S,3R,4S,5R,6R)-6-acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxymethyl]-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester 
• 178621-92-6 (2R,3S,5R,6S)-5-Benzyloxy-6-methoxy-2-[(2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxymethyl]-tetrahydro-pyran-3-ol 
• 178621-85-7 Benzoic acid (2R,3S,5R,6S)-5-benzyloxy-6-methoxy-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trimethylsilanyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester 
• 178621-82-4 Benzoic acid (2R,3S,5R,6S)-2-((2S,3R,4S,5R,6R)-6-acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester 
• 178621-83-5 Benzoic acid (2R,3S,5R,6S)-5-benzyloxy-6-methoxy-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester 
• 178621-86-8 Benzoic acid (2R,3S,5R,6S)-2-((2S,3R,5S,6R)-6-acetoxymethyl-3,5-bis-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester 
• 178621-84-6 (2R,3S,5R,6S)-5-Benzyloxy-6-methoxy-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-ol 
• 178621-88-0 (2R,3S,5R,6S)-5-Benzyloxy-2-((2S,3R,5S,6R)-3,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol 
• 178621-77-7 Benzoic acid (2R,3S,5R,6S)-2-acetoxymethyl-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

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.

Total synthesis of actinobolin from d-glucose by way of the stereoselective three-component coupling reaction

The total synthesis of (-)-actinobolin 3, an antipode of the natural product, starting from d-glucose is described. A three-component coupling reaction of functionalized cyclohexenone (+)-6 derived from d-glucose by way of Ferrier's carbocyclization react

Stereoselective synthesis of the fully functionalized HIJ-ring framework of ciguatoxin

An efficient convergent synthetic route to construct the HIJ-ring system of ciguatoxin was achieved via stereo controlled eight-membered ring formation by using acetylene cobalt complex and subsequent six-membered ring formation through intramolecular 1,4-addition reaction.

Synthesis of JKLM ring fragment of ciguatoxin via acetylene-cobalt strategy

A stereoselective synthesis of the JKLM ring fragment has been achieved through a coupling between two segments via heteroconjugate addition, seven-membered ether ring formation mediated by an acetylene cobalt complex and spiroketalization reaction.

Synthesis of the JKLM-ring fragment of ciguatoxin

A stereoselective synthesis of the LM-ring fragment has been achieved starting from a sugar derivative. A stereoselective synthesis of the JKLM-ring fragment has been achieved through a coupling between two segments via heteroconjugate addition, seven-membered ether ring formation mediated by an acetylene cobalt complex, and spiroketalization reaction.

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.

Synthesis of a 3-deoxy-L-iduronic acid containing heparin pentasaccharide to probe the conformation of the antithrombin III binding sequence

We report in this work the total synthesis of a close analogue of the pentasaccharide active site of heparin, in which the l-iduronic acid residue has been deoxygenated at position three. 1H NMR studies demonstrated that, as anticipated, such a modification induces a shift of the conformational equilibrium toward 1C4 (contribution to the conformational equilibrium rises from 37% to 65%) and a substantial decrease of the affinity for antithrombin III (K(d) 0.154μM versus 0.050μM). Copyright (C) 1998 Elsevier Science Ltd.

Synthesis of the methyl α-glycosides of some isomalto-oligosaccharides specifically deoxygenated at position C-3

Methyl α-isomaltoside and methyl α-isomaltotrioside specifically deoxygenated at position C-3 of various glucopyranosyl units were synthesized by condensation of either 1,6-di-O-acetyl-2,4-di-O-benzyl-3-deoxy-α,β-D-ribo-hexopyranose (7) or 1,6-di-O-acetyl