5158-60-1

Basic information

• Product Name: methyl 6-deoxy-3-O-methyl-α-L-mannopyranoside
• CAS NO: 5158-60-1
• Molecular Weight: 192.212
• Mol File: 5158-60-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: methyl 6-deoxy-3-O-methyl-α-L-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 6-deoxy-3-O-methyl-α-L-mannopyranoside(5158-60-1)
• EPA Substance Registry System: methyl 6-deoxy-3-O-methyl-α-L-mannopyranoside(5158-60-1)

Safety Data

• Hazardous Substances Data: 5158-60-1(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 3615-41-6 L-Rhamnose 
• 18276-53-4 1-(trimethylsilyl)-1H-pyrrole 
• 14133-63-2 methyl 2,3-O-isopropylidene-α-L-rhamnoside 
• 61199-76-6 methyl 4-O-benzyl-endo-2,3-O-benzylidene-α-L-rhamnopyranoside 
• 69850-47-1 (2R,3R,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol 
• 25019-69-6 methyl 4-O-benzyl-α-L-rhamnopyranoside 
• 301828-99-9 methyl 6-deoxy-4-O-pivaloyl-α-L-mannopyranoside 
• 33647-67-5 (S)-1-(2,5-dihydro-2,5-dimethoxy-2-furyl)ethanol 
• 55102-47-1 methyl 2,3,6-trideoxy-β-L-glycero-hex-2-enopyranosid-4-ulose 
• 4208-64-4 (S)-1-(2-furanyl)ethanol 

Downstream Products

• 112047-81-1 O³-methyl-D-ribo-6-deoxy-[2]hexosulose-bis-phenylhydrazone 
• 56083-41-1 methyl 2,4-di-O-acetyl-3-O-methyl-α-L-rhamnopyranoside 
• 523-74-0 O³-methyl-6-deoxy-D-altrose 

Relevant articles and documents

Mandelalides A-D, cytotoxic macrolides from a new Lissoclinum species of South African tunicate

Mandelalides A-D are variously glycosylated, unusual polyketide macrolides isolated from a new species of Lissoclinum ascidian collected from South Africa, Algoa Bay near Port Elizabeth and the surrounding Nelson Mandela Metropole. Their planar structures were elucidated on submilligram samples by comprehensive analysis of 1D and 2D NMR data, supported by mass spectrometry. The assignment of relative configuration was accomplished by consideration of homonuclear and heteronuclear coupling constants in tandem with ROESY data. The absolute configuration was assigned for mandelalide A after chiral GC-MS analysis of the hydrolyzed monosaccharide (2-O-methyl-α-l-rhamnose) and consideration of ROESY correlations between the monosaccharide and aglycone in the intact natural product. The resultant absolute configuration of the mandelalide A macrolide was extrapolated to propose the absolute configurations of mandelalides B-D. Remarkably, mandelalide B contained the C-4′ epimeric 2-O-methyl-6- dehydro-α-l-talose. Mandelalides A and B showed potent cytotoxicity to human NCI-H460 lung cancer cells (IC50, 12 and 44 nM, respectively) and mouse Neuro-2A neuroblastoma cells (IC50, 29 and 84 nM, respectively).

Regioselective methylation of methyl glycopyranosides with diazomethane in the presence of transition-metal chlorides and of boric acid

Partial methylation of the methyl pyranosides of a number of pentoses, hexoses, 6-deoxyhexoses, methyl uronates and their methyl ethers with diazomethane in the presence of transition-metal chlorides and boric acid was studied. It was found for methyl glycosides of pentoses and 6-deoxyhexoses that tin(II), antimony(III), and titanium(IV) chlorides as well as boric acid promoted substitution mainly of OH-3, but with cerium(III) and zinc(II) salts mainly substitution of OH-2 was observed. Methylation of methyl β-l-rhamnopyranoside demonstrated higher reactivity of OH-2 in all cases. The methylation of methyl glycosides of hexoses in the presence of tin(II), antimony(III) and cerium(III) chlorides gave mainly 3-methyl ethers. The 3-methyl ethers, which are not involved in further complexation, accumulated up to 50-80% of the reaction mixture (95-100% of monomethyl ether fraction). Convenient preparative syntheses of methyl ethers for a number of sugars are suggested. Copyright (C) 1999 Elsevier Science Ltd.

Synthesis of acofriose, a constituent sugar of the lipopolysaccharide of a smooth strain of Pseudomonas syringae pv. phaseolicola, race 2

The sugar composition of the lipopolysaccharide (LPS) of a smooth strain of Pseudomonas syringae pv. phaseolicola, race 2 has been determined.Rhamnose, fucose, acofriose(3-O-methyl-L-rhamnose) and glucose have been found to be the main constituent of the sugar chain of the LPS.For unequivocal characterization of acofriose by chromatographic technique, it has been synthesized by a convenient procedure in two steps.