34299-65-5

Basic information

• Product Name: Methyl 6-deoxy-β-L-idopyranoside
• Synonyms: Methyl 6-deoxy-β-L-idopyranoside
• CAS NO: 34299-65-5
• Molecular Formula: C₇H₁₄O₅
• Molecular Weight: 178.18306
• Mol File: 34299-65-5.mol
• Article Data: 51

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 6-deoxy-β-L-idopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 6-deoxy-β-L-idopyranoside(34299-65-5)
• EPA Substance Registry System: Methyl 6-deoxy-β-L-idopyranoside(34299-65-5)

Safety Data

• Hazardous Substances Data: 34299-65-5(Hazardous Substances Data)

Upstream product

• 111476-43-8 methyl β-D-glucopyranoside 6-phenylthionocarbonate 
• 53942-13-5 Methyl 2,3,4-Tri-O-acetyl-6-deoxy-β-D-galactopyranoside 
• 67-56-1 methanol 
• 6189-71-5 α-D-fucose 
• 100201-60-3 sophoraflavoside I 
• 19057-61-5 parillin 
• 24332-93-2 Δ(20(22))-sarsaparilloside 
• 24333-07-1 sarsaparilloside 
• 1374788-87-0 3-O-{[α-L-rhamnopyranosyl(1->4)][β-D-glucopyranosyl(1->6)]-β-D-glucopyranosyl}-26-O-β-D-glucopyranosyl-(25S)-5β-furostane-3β,22,26-triol 
• 80681-50-1 C₃₀H₅₁NO₂₅ 
• 80681-51-2 C₂₄H₄₁NO₂₁ 

Downstream Products

• 14064-39-2 L-galacto-2,4,5-Trihydroxy-3-methoxy-hexanal 
• 3615-37-0 D-Fucose 
• 135041-33-7 methyl 3-O-benzyl-β-L-fucopyranoside 
• 14686-83-0 C₂₁H₂₂O₇ 
• 87171-57-1 methyl 2,3,4-tri-O-(p-bromobenzoyl)-β-L-fucopyranoside 
• 134645-97-9 methyl 2,3-di-O-benzoyl-6-deoxy-β-D-galactopyranoside 
• 171228-79-8 Methyl 3,4-O-(R)-benzylidene-6-deoxy-β-L-galactopyranoside 
• 171228-78-7 Methyl 3,4-O-(S)-benzylidene-6-deoxy-β-L-galactopyranoside 
• 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 
• 170998-60-4 Methyl 2-O-acetyl-4-O-benzoyl-6-deoxy-β-L-galactopyranoside 

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 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.

Catalytic and regioselective oxidation of carbohydrates to synthesize keto-sugars under mild conditions

A new catalytic and regioselective approach for the synthesis of keto-sugars is described. An organotin catalyst, Oc2SnCl2, in the presence of trimethylphenylammonium tribromide ([TMPhA]+Br3-) accelerates the regioselective oxidation at the axial -OH group of 1,2-diol moieties in galactopyranosides. The reaction conditions can also be used for the regioselective oxidation of various carbohydrates.