5155-43-1

Basic information

• Product Name: METHYL-6-DEOXY-A-D-GLUCOPYRANOSIDE
• Synonyms: METHYL-6-DEOXY-A-D-GLUCOPYRANOSIDE;A3, A6-MANNOPENTAOSE;Methyl 6-broMo-6-deoxy-α-D-glucopyranoside;(2S,3R,4S,5S,6R)-2-methoxy-6-methyloxane-3,4,5-triol
• CAS NO: 5155-43-1
• Molecular Formula: C₇H₁₄O₅
• Molecular Weight: 178.18306
• Mol File: 5155-43-1.mol
• Article Data: 63

Chemical Properties

• Appearance: /
• Storage Temp.: ?20°C
• CAS DataBase Reference: METHYL-6-DEOXY-A-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL-6-DEOXY-A-D-GLUCOPYRANOSIDE(5155-43-1)
• EPA Substance Registry System: METHYL-6-DEOXY-A-D-GLUCOPYRANOSIDE(5155-43-1)

Safety Data

• Hazardous Substances Data: 5155-43-1(Hazardous Substances Data)

Usage

General Description

Methyl-6-deoxy-α-D-glucopyranoside is a chemical compound that belongs to the group of glycosides, which are organic compounds containing a sugar molecule bonded to another group through a glycosidic linkage. METHYL-6-DEOXY-A-D-GLUCOPYRANOSIDE is derived from glucose and has a methyl group attached to the sixth carbon of the sugar ring. It is commonly used in organic synthesis, particularly in the preparation of various glycosides and as a building block for the synthesis of complex natural products and pharmaceuticals. Methyl-6-deoxy-α-D-glucopyranoside has also been investigated for its potential use in carbohydrate chemistry and biochemistry research.

Upstream product

• 67-56-1 methanol 
• 2438-80-4 L-Fucose 
• 73-34-7 6-deoxy-L-galactose 
• 73139-33-0 methyl-2,3-di-O-acetyl-4-O-benzoyl-6-desoxy-α-D-arabino-hex-5-enopyranoside 
• 24332-97-6 Methyl 2,3,4-tri-O-acetyl-6-deoxy-β-L-galactopyranoside 
• 7647-01-0 hydrogenchloride 
• 16741-27-8 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide 
• 4148-58-7 (4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 2774-23-4 methyl 2-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 111476-43-8 methyl β-D-glucopyranoside 6-phenylthionocarbonate 
• 19940-17-1 methyl 2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranoside 
• 7465-44-3 methyl 6-bromo-6-deoxy-α-D-glucopyranoside 
• 5155-46-4 methyl 6-iodo-6-deoxy-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 

Downstream Products

• 14064-39-2 L-galacto-2,4,5-Trihydroxy-3-methoxy-hexanal 
• 3615-37-0 D-Fucose 
• 88331-96-8 methyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 89202-43-7 methyl 2,4-di-O-benzoyl-3-O-benzyl-α-L-rhamnopyranoside 
• 139760-16-0 Methyl O-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-α-D-galactopyranoside 
• 139760-05-7 Methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 139760-06-8 O-(2,3,4-Tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl chloride 
• 139869-57-1 C₅₉H₅₇ClO₂₁ 
• 139760-15-9 Methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside 
• 139760-12-6 C₆₁H₆₀O₂₃ 
• 6893-93-2 methyl 2,3-di-O-benzoyl-6-deoxy-4-O-(p-tolylsulfonyl)-α-D-glucopyranoside 
• 14133-63-2 methyl 2,3-O-isopropylidene-α-L-rhamnoside 
• 1379777-16-8 methyl 3-O-phenoxythiocarbonyl-β-L-fucopyranoside 
• 1399293-50-5 methyl 3-O-(3,5-difluorobenzensulfonyl)-β-L-fucopyranoside 

Relevant articles and documents

Calcium hypophosphite mediated deiodination in water: Mechanistic insights and applications in large scale syntheses of d-quinovose and d-rhamnose

The inorganic calcium hypophosphite was found to be a cheap, non-toxic, water-soluble and environmentally friendly reducing reagent for radical deiodination in water. Thorough mechanism studies revealed that calcium hypophosphite was oxidized to water insoluble calcium phosphite which was the major co-product of the deiodination reaction. Based on this observation, a practical synthesis of rare d-quinovose and d-rhamnose from cheap and commercially available materials on a hundred-mmol scale was reported.

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 β-(1→2)-Linked 6-Deoxy- l -altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor

The β-(1→2)-linked 6-deoxy-l-altropyranose di- to pentasaccharides 2-5, relevant to the O-antigen of the infectious Yersinia enterocolitica O:3, were synthesized for the first time. The challenging 1,2-cis-altropyranosyl linkage was assembled effectively via glycosylation with 2-O-benzyl-3,4-di-O-benzoyl-6-deoxy-l-altropyranosyl ortho-hexynylbenzoate (7) under the catalysis of PPh3AuNTf2. NMR and molecular modeling studies showed that the pentasaccharide (5) adopted a left-handed helical conformation.