65982-18-5

Basic information

• Product Name: Acetic acid (2S,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-chloro-tetrahydro-pyran-4-yl ester
• CAS NO: 65982-18-5
• Molecular Weight: 366.752
• Mol File: 65982-18-5.mol
• Article Data: 31

Chemical Properties

• CAS DataBase Reference: Acetic acid (2S,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-chloro-tetrahydro-pyran-4-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid (2S,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-chloro-tetrahydro-pyran-4-yl ester(65982-18-5)
• EPA Substance Registry System: Acetic acid (2S,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-chloro-tetrahydro-pyran-4-yl ester(65982-18-5)

Safety Data

• Hazardous Substances Data: 65982-18-5(Hazardous Substances Data)

Upstream product

• 83-87-4 β-D-mannopyranose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 604-70-6 methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 507-09-5 tiolacetic acid 
• 83-87-4 D-Mannose pentaacetate 
• 3458-28-4 D-Mannose 
• 75-36-5 acetyl chloride 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 36868-85-6 4-chlorophenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 6763-46-8 2,3,4,5,6-Penta-O-acetyl-D-galaktose 
• 439-03-2 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl fluoride 

Downstream Products

• 28538-11-6 (1S)-1-(4-methoxy-phenyl)-1,5-anhydro-D-mannitol 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 129948-14-7 methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 122999-08-0 trimethylsilyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 117252-67-2 2-(Trimethylsilyl)ethyl-<2,3,4,6-tetra-O-acetyl-α-D-mannopyranosid> 
• 130471-79-3 4-O-Benzoylphloracetophenone 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside) 
• 77593-34-1 7-bromo-3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-2-naphth-o-anisidide 
• 102871-19-2 1,6-anhydro-3,4-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-L-gulopyranose 
• 68736-77-6 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside 
• 93220-80-5 C₁₄H₁₉O₉ 
• 172364-85-1 methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 
• 2873-29-2 D-glucal triacetate 
• 57884-82-9 2,3,4,6-tetra-O-acetyl-β-D-mannopyranose 
• 22860-22-6 2,3,4,6-tetra-O-acetyl-α-D-mannopyranose 

Relevant articles and documents

Reaction of some 1,2-trans-aldose peracetates with thionyl chloride-acetic acid - a convenient synthesis of some 1,2-trans-per-O-acetyl-D-glycosyl chlorides

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Chemoenzymatic synthesis of arabinomannan (AM) glycoconjugates as potential vaccines for tuberculosis

Mycobacteria infection resulting in tuberculosis (TB) is one of the top ten leading causes of death worldwide in 2018, and lipoarabinomannan (LAM) has been confirmed to be the most important antigenic polysaccharide on the TB cell surface. In this study, a convenient synthetic method has been developed for synthesizing three branched oligosaccharides derived from LAM, in which a core building block was prepared by enzymatic hydrolysis in flow chemistry with excellent yield. After several steps of glycosylations, the obtained oligosaccharides were conjugated with recombinant human serum albumin (rHSA) and the ex-vivo ELISA tests were performed using serum obtained from several TB-infected patients, in order to evaluate the affinity of the glycoconjugate products for the human LAM-antibodies. The evaluation results are positive, especially compound 21 that exhibited excellent activity which could be considered as a lead compound for the future development of a new glycoconjugated vaccine against TB.

Synthesis of glycosyl chlorides using catalytic Appel conditions

The stereoselective synthesis of glycosyl chlorides using catalytic Appel conditions is described. Good yields of α-glycosyl chlorides were obtained using a range of glycosyl hemiacetals, oxalyl chloride and 5 mol% Ph3PO. For 2-deoxysugars treatment of the corresponding hemiacetals with oxalyl chloride without phosphine oxide catalyst also gave good yields of glycosyl chloride. The method is operationaly simple and the 5 mol% phosphine oxide by-product can be removed easily. Alternatively a one-pot, multi-catalyst glycosylation can be carried out to transform the glycosyl hemiacetal directly to a glycoside.