13964-22-2

Basic information

• Product Name: 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• Synonyms: 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• CAS NO: 13964-22-2
• Molecular Weight: 364.395
• Mol File: 13964-22-2.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose(13964-22-2)
• EPA Substance Registry System: 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose(13964-22-2)

Safety Data

• Hazardous Substances Data: 13964-22-2(Hazardous Substances Data)

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 582-25-2 Potassium benzoate 
• 98-88-4 benzoyl chloride 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 591727-19-4 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 85909-02-0 N-benzyl-N-(tert-butoxycarbonyl)-benzamide 
• 99605-27-3 3-O-(tert-butyldimethylsilyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 130132-25-1 (3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-(2-phenyl-benzo[1,3]dithiol-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxole 
• 78730-56-0 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose potassium salt 

Downstream Products

• 149402-97-1 Benzoic acid (3aR,5R,6S,6aR)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 1333476-11-1 diethyl (4R)-[3-O-acetyl-2-O-benzoyl-1-(4-N-benzoylcytosin-1-yl)-1-deoxy-α-D-threofuranos-4-yl]phosphonate 
• 1333476-10-0 diethyl (4R)-[3-O-acetyl-2-O-benzoyl-1-deoxy-1-(thymin-1-yl)-α-D-threofuranos-4-yl]phoshonate 
• 1333476-08-6 diethyl (4R)-(1,3-di-O-acetyl-2-O-benzoyl-α-D-threofuranos-4-yl)phosphonate 
• 124061-89-8 3-O-benzoyl-1,2-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 
• 1038619-65-6 C₂₀H₂₆O₇ 

Relevant articles and documents

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Thioglucose compound and preparation method thereof

The invention provides a thioglucose compound which has the following general formula: Wherein R is selected from H or acetyl. The preparation method of the thioglucose compound is easy to obtain, low in production cost and suitable for industrial product

Zn-Catalyzed tert-Butyl Nicotinate-Directed Amide Cleavage as a Biomimic of Metallo-Exopeptidase Activity

A two-step catalytic amide-to-ester transformation of primary amides under mild reaction conditions has been developed. A tert-butyl nicotinate (tBu nic) directing group is easily introduced onto primary amides via Pd-catalyzed amidation with tert-butyl 2-chloronicotinate. A weak base (Cs2CO3 or K2CO3) at 40-50 °C can be used provided that 1,1′-bis(dicyclohexylphosphino)ferrocene is selected as ligand. The tBu nic activated amides subsequently allow Zn(OAc)2-catalyzed nonsolvolytic alcoholysis in tBuOAc at 40-60 °C under neutral reaction conditions. The activation mechanism is biomimetic: the C3-ester substituent of the pyridine in the directing group populates the trans-conformer suitable for Zn-chelation, C=Oamide-Zn-Ndirecting group, and Zn-coordinated alcohol is additionally activated as a nucleophile by hydrogen bonding with the acetate ligand of the catalyst. Additionally, the acetate ligand assists in intramolecular O-to-N proton transfer. The chemoselectivity versus other functional groups and compatibility with challenging reaction partners, such as peptides, sugars, and sterols, illustrates the synthetic applicability of this two-step amide cleavage method. The tBu nic amides do not require purification before cleavage. Preliminary experiments also indicate that other weak nucleophiles can be used such as (hetero)arylamines (transamidation) as exemplified by 8-aminoquinoline.