14218-10-1

Basic information

• Product Name: 1,5-anhydro-tetra-O-benzoyl-D-glucitol
• Synonyms: 1,5-anhydro-tetra-O-benzoyl-D-glucitol
• CAS NO: 14218-10-1
• Molecular Weight: 580.591
• Mol File: 14218-10-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1,5-anhydro-tetra-O-benzoyl-D-glucitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-anhydro-tetra-O-benzoyl-D-glucitol(14218-10-1)
• EPA Substance Registry System: 1,5-anhydro-tetra-O-benzoyl-D-glucitol(14218-10-1)

Safety Data

• Hazardous Substances Data: 14218-10-1(Hazardous Substances Data)

Upstream product

• 32849-03-9 methyl 2,3,4,6-tetra-O-benzoyl-α-D-glycopyranoside 
• 27518-98-5 1,5-anhydro-D-altritol 
• 172847-85-7 (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 103664-30-8 3,4,6-tri-O-benzoyl-1,2-O-benzylidene-α-D-glucopyranose 
• 78890-68-3 1-deoxy-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 107-13-1 acrylonitrile 

Downstream Products

• 80245-23-4 1,5-anhydro-2,4,6-tri-O-benzoyl-D-glucitol 
• 74629-56-4 1,5-anhydro-3,4,6-tri-O-benzoyl-D-glucitol 
• 154-58-5 1,5-anhydro-D-glucitol 

Relevant articles and documents

Investigating the rate of photoreductive glucosyl radical generation

Chemical equations presented. The photoreduction of glucosyl halides to generate glucosyl radicals has been investigated to probe the nature of the photoredox cycle. Amine (the reductant) and catalyst concentration affect the reaction rate at low concentrations but exhibit saturation at higher concentrations. Water and hydrophobic catalysts were found to significantly increase the conversion efficiency.

A highly stereoselective synthesis of α-Linked C-glycopyranosides using 2,2'-azobis-(2,4-dimethyl-4-methoxyvaleronitrile) (V-70)

α-Linked C-glycopyranosides were obtained effectively by the radical addition reaction using V-70, an effective radical initiator under mild conditions.

NaBH3CN and other systems as substitutes of tin and silicon hydrides in the light or heat-initiated reduction of halosugars: A tunable access to either 2-deoxy sugars or 1,5-anhydro-itols

UV light-promoted reduction of acetobromoglucose by NaBH3CN in t-BuOH afforded 1,3,4,6-tetra-O-acetyl-2-deoxy-α-d-arabino-hexopyranose in high yield and purity, via a Surzur-Tanner rearrangement, while, with 10 mol % thiophenol added, acetylated 1,5-anhydro-d-glucitol was cleanly obtained. Such tin-free and mild reductions, presumed to proceed via radical pathways, were more efficient with NaBH3CN compared to NaBH4 or NaBD 4, and do not occur with acetochloroglucose. Similar reductions to 1,3,4,6-tetra-O-acetyl-2-deoxy-α-d-arabino-hexopyranose were achieved upon heating to 80 C t-BuOH or CH3CN solutions of NaBH3CN and AIBN, but with a lower selectivity due to competing ionic reactions. With other pyranosyl bromides, reductions by NaBH3CN could be tuned similarly (d-galacto), but some (d-manno, 5-thio-d-xylo) gave mainly or exclusively 1,5-anhydro-itols. Other conditions, or reagents promoting SET process, afforded also reduced products, but with lower rates or selectivities. Primary iodides were reduced readily with NaBH3CN under UV light.

A novel and efficient method for the oxidative removal of O-benzyl protective groups of carbohydrates by tetrabutylammonium peroxydisulfate

Various benzyl ethers of carbohydrates have been selectively oxidized to the corresponding benzoate esters 2a-j with tetrabutylammonium peroxydisulfate under neutral conditions followed by debenzoylation with sodium methoxide to afford the debenzylated carbohydrates 3a-j in good overall yields. Noteworthy is that highly chemoselective reactions were achieved with the co-existence of other functionalities. Thieme Stuttgart.