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 
• 24332-97-6 Methyl 2,3,4-tri-O-acetyl-6-deoxy-β-L-galactopyranoside 
• 7647-01-0 hydrogenchloride 
• 6340-57-4 methyl 2,3,4-tri-O-acetyl-6-deoxy-β-D-glucopyranoside 
• 7404-26-4 methyl 6-bromo-6-deoxy-β-D-glucopyranoside 
• 19940-17-1 methyl 2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranoside 
• 51236-53-4 methyl 2,3,4-tri-O-benzoyl-6-deoxy-α-D-glucopyranoside 
• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 
• 1012796-69-8 C₁₆H₂₄O₇ 
• 141-52-6 sodium ethanolate 
• 1012796-77-8 C₁₆H₂₄O₇ 
• 1012796-81-4 C₁₆H₂₄O₇ 

Downstream Products

• 14064-39-2 L-galacto-2,4,5-Trihydroxy-3-methoxy-hexanal 
• 3615-37-0 D-Fucose 
• 134311-92-5 methyl-2,4-di-O-benzyl-β-D-quinovopyranoside 
• 176380-03-3 methyl 2,3‐di‐O‐benzyl‐6‐deoxy‐β‐D‐glucopyranoside 
• 197657-27-5 methyl-2-O-benzyl-β-D-quinovopyranoside 
• 51288-33-6 C₂₁H₂₂O₇ 
• 51236-57-8 C₂₁H₂₂O₇ 
• 15830-76-9 methyl 2,3,4-tri-O-acetyl-6-deoxy-α-D-talopyranoside 
• 4860-85-9 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 14133-63-2 methyl 2,3-O-isopropylidene-α-L-rhamnoside 
• 1379777-16-8 methyl 3-O-phenoxythiocarbonyl-β-L-fucopyranoside 
• 1128-40-1 methyl 6-deoxy-β-L-glucopyranoside 
• 75336-82-2 Methyl 3-O-benzyl-α-L-rhamnopyranoside 
• 1399293-50-5 methyl 3-O-(3,5-difluorobenzensulfonyl)-β-L-fucopyranoside 

Relevant articles and documents

Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation

A Cu(II)-catalyzed diastereoselective Michael/aldol cascade approach is used to accomplish concise total syntheses of cardiotonic steroids with varying degrees of oxygenation including cardenolides ouabagenin, sarmentologenin, 19-hydroxysarmentogenin, and 5-epi-panogenin. These syntheses enabled the subsequent structure activity relationship (SAR) studies on 37 synthetic and natural steroids to elucidate the effect of oxygenation, stereochemistry, C3-glycosylation, and C17-heterocyclic ring. Based on this parallel evaluation of synthetic and natural steroids and their derivatives, glycosylated steroids cannogenol-l-α-rhamnoside (79a), strophanthidol-l-α-rhamnoside (92), and digitoxigenin-l-α-rhamnoside (97) were identified as the most potent steroids demonstrating broad anticancer activity at 10-100 nM concentrations and selectivity (nontoxic at 3 μM against NIH-3T3, MEF, and developing fish embryos). Further analyses indicate that these molecules show a general mode of anticancer activity involving DNA-damage upregulation that subsequently induces apoptosis.

Synthesis of Deoxyglycosides by Desulfurization under UV Light

This study was performed to develop a highly efficient method whereby desulfurization could be completed in 0.5 h under ultraviolet light, at room temperature, and in the presence of trialkylphosphine. Using this method, deoxyglycosides could be produced from sulfur-containing glycosides in almost quantitative yields. The much higher reactivity of desulfurization with triethylphosphine versus that with triethylphosphite is also discussed.

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.