52612-68-7

Basic information

• Product Name: methyl 4,6-O-benzylidene-2-deoxyhexopyranoside
• Synonyms: Methyl 4,6-O-benzylidene-2-deoxyhexopyranoside
• CAS NO: 52612-68-7
• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.2897
• Mol File: 52612-68-7.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 434.2°C at 760 mmHg
• Flash Point: 216.4°C
• Density: 1.27g/cm³
• Vapor Pressure: 2.61E-08mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: methyl 4,6-O-benzylidene-2-deoxyhexopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-O-benzylidene-2-deoxyhexopyranoside(52612-68-7)
• EPA Substance Registry System: methyl 4,6-O-benzylidene-2-deoxyhexopyranoside(52612-68-7)

Safety Data

• Hazardous Substances Data: 52612-68-7(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 67308-47-8 methyl-(α-D-xylo-2-deoxy-hexopyranoside) 
• 2880-96-8 methyl 2,3-anhydro-4,6-dioxabenzylidene-α-D-gulopyranose 
• 79015-45-5 methyl-[O⁴,O⁶((S)-benzylidene)-S-methyl-2-thio-α-D-idopyranoside] 
• 64-17-5 ethanol 
• 86420-68-0 methyl 4,6-O-benzylidene-α-D-galactopyranoside 3-O-p-toluenesulfonate 
• 13145-22-7 methyl 2-deoxy-α-D-glucopyranoside 
• 74984-85-3 methyl-4,6-O-phenylmethylene-2,3-thionocarbonyl-α-D-mannopyranoside 
• 70774-92-4 methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside 
• 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 

Downstream Products

• 21090-92-6 methyl-[O⁴,O⁶-((S)-benzylidene)-O³-methyl-α-D-xylo-2-deoxy-hexopyranoside] 
• 94124-61-5 tert-Butyl-methoxy-((2S,4aR,6S,8S,8aR)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-phenyl-silane 
• 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 
• 182276-82-0 methyl 4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside 
• 93960-50-0 Benzoic acid (2S,3S,4S,6S)-2-bromomethyl-3-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester 
• 119943-96-3 Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside 
• 872182-66-6 methyl 4-O-benzyl-2-deoxy-α-D-ribo-hexopyranoside 

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.

Synthesis of ribo-hexopyranoside- and altrose-based azacrown ethers and their application in an asymmetric Michael addition

The synthesis of four new ribo-hexopyranoside-based chiral lariat ethers of monoaza-15-crown-5 type and two altropyranoside-based crown ethers were elaborated. Our syntheses utilized the regioselective ring opening of the oxiran moiety of the 2,3-anhydro sugars by nucleophilic reagents to afford the key intermediates. The reaction of methyl-2,3-anhydro-4,6-O-benzylidene-α-d- mannopyranoside with ethanolamine is especially of interest to afford a 3-substituted altropyranoside. One of the ribo-hexopyranoside-based lariat ethers with a 4-methoxyphenyl substituent induced an enantioselectivity of 80% when used as catalyst in the Michael addition of diethyl acetamidomalonate to trans-β-nitrostyrene under phase transfer catalytic conditions.