56225-80-0

Basic information

• Product Name: Benzoic acid (3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester
• CAS NO: 56225-80-0
• Molecular Weight: 452.415
• Mol File: 56225-80-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzoic acid (3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid (3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester(56225-80-0)
• EPA Substance Registry System: Benzoic acid (3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester(56225-80-0)

Safety Data

• Hazardous Substances Data: 56225-80-0(Hazardous Substances Data)

Upstream product

• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 65-85-0 benzoic acid 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-68-2 α-D-glucopyranose peracetylate 
• 604-69-3 β-D-glucose pentaacetate 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 78942-86-6 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-α-D-glucopyranose 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 81342-44-1 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 93-97-0 benzoic acid anhydride 

Relevant articles and documents

Highly efficient β-glucosylation of the acidic hydroxyl groups, phenol and carboxylic acid, with an peracetylated glucosyl fluoride using a combination of BF3·Et2O and DTBMP as a promoter

A combination of BF3·Et2O and DTBMP was established to be an efficient promoter of β-glucosylation of both phenols and carboxylic acids with a peracetylated glucosyl fluoride (2). This new method achieved remarkably high yields and β

Phyllanthoside-Phyllanthostatin Synthetic Studies. 8. Total Synthesis of (+)-Phyllanthoside. Development of the Mitsunobu Glycosyl Ester Protocol

The first total syntheses of the antineoplastic glycoside (+)-phyllanthoside (1) and the parent disaccharide (-)-phyllanthose (5) have been achieved. Stereoselective Koenigs-Knorr coupling of two 6-deoxyglucose derivatives, bromide 54 and alcohol 55, generated the uncommon 1′ → 2β glycosidic linkage of (-)-phyllanthose. A stereochemically convergent Mitsunobu reaction of protected disaccharide 87 with aglycon carboxylic acid 80, prepared via asymmetric synthesis, then led to 1 of high enantiomeric purity. The Mitsunobu procedure comprises an efficient general method for stereospecific assembly of β-glycosyl esters.

Synthesis of Glycosyl Trifluoroacetates and Their Reactions with Carboxylic Acids

2,3,4,6-Tetra-O-acetyl-1-O-trifluoroacetyl-α-D-glucopyranose was prepared in high yield by treating 1,2,3,4,6-penta-O-acetyl-α- or -β-D-glucopyranose with a mixture of trifluoroacetic acid and its anhydride in the presence of trifluoromethanesulfonic acid or antimony (V) fluoridegraphite catalyst.The reaction of the trifluoroacetate with some carboxylic acids afforded the corresponding 1-O-acyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoses.By a similar procedure, anomeric 1-O-trifluoroacetyl-2,3,5-tri-O-benzoyl- and -2,3,5-tri-O-acetyl-D-ribofuranose were obtained from 1-O-acetyl-2,3,5-tri-O-benzoyl- and 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose respectively, and these trifluoroacetates were allowed to react with some carboxylic acids to yield the corresponding 1-O-acyl-β-D-ribofuranose benzoates and acetates.These products were also prepared by direct fusion of 1-O-acetyl-β-D-ribofuranose benzoate and acetate with carboxylic acids.Keywords-glycosyl trifluoroacetate; glycosyl carboxylate; fusion reaction; tetra-O-acetyl-α-D-glucopyranosyl trifluoroacetate; tri-O-benzoyl-α,β-D-ribofuranosyl trifluoroacetate; tri-O-acetyl-α,β-D-ribofuranosyl trifluoroacetate