6752-48-3

Basic information

• Product Name: 1-O-Methyl-4-O,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranose
• Synonyms: 1-O-Methyl-4-O,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranose;Methyl 4-O,6-O-(phenylmethylene)-2-deoxy-α-D-arabino-hexopyranoside
• CAS NO: 6752-48-3
• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.28972
• Mol File: 6752-48-3.mol
• Article Data: 33

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-O-Methyl-4-O,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-Methyl-4-O,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranose(6752-48-3)
• EPA Substance Registry System: 1-O-Methyl-4-O,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranose(6752-48-3)

Safety Data

• Hazardous Substances Data: 6752-48-3(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 67308-47-8 methyl-(α-D-xylo-2-deoxy-hexopyranoside) 
• 79015-45-5 methyl-[O⁴,O⁶((S)-benzylidene)-S-methyl-2-thio-α-D-idopyranoside] 
• 64-17-5 ethanol 
• 13145-22-7 methyl 2-deoxy-α-D-glucopyranoside 
• 74984-85-3 methyl-4,6-O-phenylmethylene-2,3-thionocarbonyl-α-D-mannopyranoside 
• 138513-06-1 methyl 4,6-O-benzylidene-2,3-O-thiocarbonyl-α-D-glucoside 
• 194149-26-3 methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 74-88-4 methyl iodide 
• 65556-00-5 methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 160400-66-8 methyl 2-deoxy-D-arabinopyranoside 
• 154-17-6 D-2-deoxyglucose 
• 6087-40-7 (2R,3S,4R,6S)-3,4-diacetoxy-2-(acetoxymethyl)-6-methoxytetrahydro-2H-pyran 

Downstream Products

• 21090-92-6 methyl-[O⁴,O⁶-((S)-benzylidene)-O³-methyl-α-D-xylo-2-deoxy-hexopyranoside] 
• 62774-38-3 Methanesulfonic acid (4aR,6R,8R,8aR)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 32469-89-9 Methyl-3-O-benzoyl-4,6-O-benzyliden-2-desoxy-α-D-arabino-hexopyranosid 
• 70717-91-8 Methyl-3-O-(4-O-acetyl-2,6-didesoxy-2-iod-3-C-methyl-α-D-mannopyranosyl)-4,6-O-benzyliden-2-desoxy-α-D-arabino-hexopyranosid 
• 78013-78-2 Methyl-4.6-O-benzyliden-3-O-(4,6-O-benzyliden-2-desoxy-2-iod-3-C-methyl-α-D-mannopyranosyl)-2-desoxy-α-D-arabino-hexopyranosid 
• 78013-78-2 Methyl-4.6-O-benzyliden-3-O-(4,6-O-benzyliden-2-desoxy-2-iod-3-C-methyl-β-D-glucopyranosyl)-2-desoxy-α-D-arabino-hexopyranosid 
• 90761-25-4 methyl 3-O-benzyl-4,6-O-benzylideno-2-deoxy-α-D-ribo-hexoside 
• 78148-01-3 methyl 3-O-benzoyl-4,6-O-benzylidene-2-deoxy-α-D-ribo-hexopyranoside 
• 63598-31-2 methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose 
• 121388-99-6 1,5-anhydro-6-O-benzyl-2-deoxy-D-ribo-hexitol 
• 872182-66-6 methyl 4-O-benzyl-2-deoxy-α-D-ribo-hexopyranoside 
• 80667-89-6 (4aR,6S,8R,8aS)-8-(benzyloxy)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine 
• 83497-33-0 methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside 
• 104872-04-0 Orlistat 

Relevant articles and documents

Reactivity–Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides

The assembly of complex bacterial glycans presenting rare structural motifs and cis-glycosidic linkages is significantly obstructed by the lack of knowledge of the reactivity of the constituting building blocks and the stereoselectivity of the reactions i

Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity

Cardiac glycosides show anticancer activities and their deoxy-sugar chains are vital for their anticancer effects. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and get more potent anticancer agents, a series of MeON-neoglycosides of digoxigenin was synthesized and evaluated. First, ten 6-deoxy- and 2,6-dideoxy-D-glucopyranosyl donors were synthesized starting from methyl α-D-glucopyranoside and 2-deoxy-D-glucose. Meanwhile, the digoxigenin was obtained by acidic hydrolysis of commercially available digoxin as glycosyl acceptor. Then, a 22-member MeON-neoglycoside library of digoxigenin was successfully synthesized by neoglycosylation method. Finally, the induction of Nur77 expression and its translocation from the nucleus to cytoplasm together with cytotoxicity of these MeON-neoglycosides were evaluated. The SAR analysis revealed that C3 glycosylation is required for their induction of Nur77 expression. Moreover, some MeON-neoglycosides (2b and 8b) could significant induce the expression of Nur77 and its translocation from the nucleus to cytoplasm. However, these compounds showed no inhibitory effects on the proliferation of cancer cells, suggesting that they may not induce apoptosis of NIH-H460 cancer cells and their underlying potential and application toward cancer cells deserves future study.

Stereoselective synthesis of α-linked 2-deoxy glycosides enabled by visible-light-mediated reductive deiodination

2-Deoxy sugars and their derivatives occur abundantly in many pharmaceutically important natural products. However, the construction of specific 2-deoxy-glycosidic bonds remains as a challenge. Herein, we report an efficient way to prepare 2-deoxy-a-glycosides by glycosylation of 2-iodo-glycosyl acetate and subsequent visible-light-mediated tin-free reductive deiodination. We have successfully applied the postglycosylational-deiodination strategy in the synthesis of more than 30 mono-, di-, tri-, tetra- and pentadeoxysaccharides with excellent stereoselectivity and efficiency. This method has also been applied to the synthesis of a 2-deoxy-tetrasac-charide containing four a-linkages.