4692-12-0

Basic information

• Product Name: .alpha.-D-Glucopyranose, 1,3,4,6-tetraacetate
• Synonyms: .alpha.-D-Glucopyranose, 1,3,4,6-tetraacetate
• CAS NO: 4692-12-0
• Molecular Formula: C₁₄H₂₀O₁₀
• Molecular Weight: 348.3
• Mol File: 4692-12-0.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: .alpha.-D-Glucopyranose, 1,3,4,6-tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: .alpha.-D-Glucopyranose, 1,3,4,6-tetraacetate(4692-12-0)
• EPA Substance Registry System: .alpha.-D-Glucopyranose, 1,3,4,6-tetraacetate(4692-12-0)

Safety Data

• Hazardous Substances Data: 4692-12-0(Hazardous Substances Data)

Upstream product

• 97-30-3 methyl-alpha-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 192753-82-5 2-O-benzyl-3,4,5,6-di-O-isopropyliclenealdehydo-L-gulose 
• 23661-29-2 phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-glucopyranoside 
• 75-05-8 acetonitrile 
• 202138-07-6 C₄₅H₆₈O₁₂ 
• 604-68-2 α-D-glucopyranose peracetylate 
• 2280-44-6 D-Glucose 

Downstream Products

• 163152-11-2 1,3,4,6-tetra-O-acetyl-2-O-<2-(chloroacetoxymethyl)benzoyl>-α-D-glucopyranose 
• 163152-25-8 O-<3,4,6-tri-O-acetyl-2-O-<2-(chloroacetoxymethyl)benzoyl>-β-D-glucopyranosyl>-(1->2)-1,3,4,6-tetra-O-acetyl-α-D-glucopyranose 
• 116912-26-6 1,3,4,6-Tetra-O-acetyl-2-O-(phenylacetyl)-α-D-glucopyranose 
• 30253-76-0 1,3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranoside 
• 7226-42-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranoside 
• 145828-18-8 3,4,6-tri-O-acetyl-2-deoxy-1-O-(diphenylphosphoryl)-α-D-arabino-hexopyranose 
• 145828-12-2 3,4,6-tri-O-acetyl-2-O-(diphenylphosphoryl)-α-D-glucopyranosyl bromide 
• 26209-93-8 5-acetoxy-2-acetoxymethyl-4H-pyran-4-one 
• 74774-04-2 3,4,6-tri-O-acetyl-2-O-(2-carboxybenzoyl)-α-D-glucopyranosyl bromide 
• 1314918-24-5 2-O-(trideuteriumacetyl)-3,4,6-tri-O-acetyl-D-glucopyranosyl ortho-hexynylbenzoate 
• 1314918-22-3 2-O-(trideuteriumacetyl)-3,4,6-tri-O-acetyl-D-glucopyranosyl ortho-hexynylbenzoate 
• 128963-04-2 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-6-(toluene-4-sulfonyloxy)-5-(2,2,2-trichloro-ethoxycarbonyloxy)-tetrahydro-pyran-4-yl ester 
• 128963-03-1 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-isopropoxycarbonyloxy-6-(toluene-4-sulfonyloxy)-tetrahydro-pyran-4-yl ester 
• 128963-02-0 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-ethoxycarbonyloxy-6-(toluene-4-sulfonyloxy)-tetrahydro-pyran-4-yl ester 

Relevant articles and documents

Photoinitiated glycosylation at 350 nm

A method for photochemical activation of glycosyl donors is presented. Selenoglycosides were activated by single-electron transfer using a photooxidant, N-methylquinolinium hexafluorophosphate, as photosensitizer and a toluene cosolvent as cosensitizer under irradiation at 350 nm. In this way we were able to synthesize glycosides including (1→6)-linked disaccharides. Benzyl ethers and benzoate esters were compatible with these conditions, allowing potentially synthetically useful transformations. The major by-products were due to hydrolysis; the reactions required the presence of oxygen and were run in air.

Carbohydrate Homologation by the Use of 2-(Trimethylsilyl)thiazole. Preparative Scale Synthesis of Rare Sugars: L-Gulose, L-Idose, and the Disaccharide Subunit of Bleomycin A2

The well established one-carbon homologation method of protected monosaccharides employing 2-(trimethylsilyl)thiazole (2-TST) as a formyl anion equivalent has been used for high yield and multigram scale synthesis of the title rare hexoses from L-xylose. Thus, L-gulose has been obtained by stereoselective anti-addition of 2-TST to aldehydo-L-xylose diacetonide followed by thiazole to formyl conversion of the resulting alcohol. The inversion of configuration at C-1 of this alcohol by an oxidation - reduction sequence prior to the aldehyde releasing from thiazole led to L-idose. The same alcohol was readily elaborated into 1,3,4,6-tetra-O-acetyl-L-gulopyranose whose highly stereoselective glycosidation coupling with 3-O-carbamoyl-2,4,6-tri-O-acetyl-α-D-mannosyl diethyl phosphate afforded the same peracetylated disaccharide subunit employed by Boger and Honda in the total synthesis of the antibiotic bleomycin A2.

An electrochemical synthesis of methyl α-isomaltoside

A novel approach has been developed for the synthesis of methyl α-isomaltoside (10), comprising, as the first step, electrochemical conversion of the hydroxyl groups of methyl α-D-glucopyranoside into the corresponding anions.The anions subsequently react with tetra-O-acetyl-α-D-glucopyranosyl bromide to give methyl 2',3',4',6'-tetra-O-acetyl-α-isomaltoside (8) as the main product.O-deacetylation of which affords 10.The glycosidation proceeds under complete stereochemical control.Keywords: Isomaltoside, methyl α-; Disaccharides; Electrochemical synthesis; Structure