14227-52-2

Basic information

• Product Name: 2,3,4,6-tetra-O-acetyl-1-chloro-β-D-mannose
• Synonyms: 2,3,4,6-tetra-O-acetyl-1-chloro-β-D-mannose
• CAS NO: 14227-52-2
• Molecular Formula: C₁₄H₁₉ClO₉
• Molecular Weight: 366.748
• Mol File: 14227-52-2.mol
• Article Data: 31

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,4,6-tetra-O-acetyl-1-chloro-β-D-mannose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-acetyl-1-chloro-β-D-mannose(14227-52-2)
• EPA Substance Registry System: 2,3,4,6-tetra-O-acetyl-1-chloro-β-D-mannose(14227-52-2)

Safety Data

• Hazardous Substances Data: 14227-52-2(Hazardous Substances Data)

Usage

General Description

2,3,4,6-tetra-O-acetyl-1-chloro-β-D-mannose is a chemical compound with the molecular formula C14H19ClO9. It is a derivative of mannose, a type of sugar, and is often used as a reagent in the synthesis of various carbohydrate derivatives. 2,3,4,6-tetra-O-acetyl-1-chloro-β-D-mannose is known for its acetyl and chloro groups, which make it a useful building block for the preparation of complex carbohydrates and glycoconjugates. Due to its synthetic versatility, 2,3,4,6-tetra-O-acetyl-1-chloro-β-D-mannose is commonly utilized in organic chemistry research and pharmaceutical development for the creation of new drugs and therapeutic agents.

Upstream product

• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 530-26-7 D-Mannose 
• 75-36-5 acetyl chloride 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 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 
• 25878-60-8 D-galactose pentaacetate 
• 4163-60-4 β-D-galactose peracetate 
• 3458-28-4 D-Mannose 
• 26189-59-3 1-chloro-1-(dimethylamino)-2-methyl-1-propene 
• 83-87-4 D-Mannose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 

Downstream Products

• 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 
• 59-56-3 mannose-1-phosphate 
• 14227-87-3 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl chloride 
• 51295-66-0 2,3,6-Tri-O-acetyl-2-O-(trichloroacetyl)-β-D-galactopyranosyl chloride 
• 28244-97-5 phenyl-1-thio-α-D-galactopyranoside 
• 1581292-47-8 m-nitrothiophenyl α-D-galactopyranoside 
• 1581292-57-0 p-nitrophenylsulfonyl α-D-galactopyranoside 
• 28512-68-7 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside 
• 1581292-46-7 C₂₀H₂₃NO₁₁S 
• 85240-45-5 4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy-1H-imidazole-5-carboxamide 

Relevant articles and documents

Zirconium tetrachloride as a convenient catalyst for the glycosylation of sterols with 2,3,4,6,6'-penta-O-acetyl-5-hydroxymethylgalactosyl fluoride

Zirconium tetrachloride was found to catalyze glycosylation of various sterols with peracetylated 5-hydroxymethylene galactosyl fluoride.

Quinoline-galactose hybrids bind selectively with high affinity to a galectin-8 N-terminal domain

Quinolines, indolizines, and coumarins are well known structural elements in many biologically active molecules. In this report, we have developed straightforward methods to incorporate quinoline, indolizine, and coumarin structures into galactoside derivatives under robust reaction conditions for the discovery of glycomimetic inhibitors of the galectin family of proteins that are involved in immunological and tumor-promoting biological processes. Evaluation of the quinoline, indolizine and coumarin-derivatised galactosides as inhibitors of the human galectin-1, 2, 3, 4N (N-terminal domain), 4C (C-terminal domain), 7, 8N, 8C, 9N, and 9C revealed quinoline derivatives that selectively bound galectin-8N, a galectin with key roles in lymphangiogenesis, tumor progression, and autophagy, with up to nearly 60-fold affinity improvements relative to methyl β-d-galactopyranoside. Molecular dynamics simulations proposed an interaction mode in which Arg59 had moved 2.5 ? and in which an inhibitor carboxylate and quinoline nitrogen formed structure-stabilizing water-mediated hydrogen bonds. The compounds were demonstrated to be non-toxic in an MTT assay with several breast cancer cell lines and one normal cell line. The improved affinity, selectivity, and low cytotoxicity suggest that the quinoline-galactoside derivatives provide an attractive starting point for the development of galectin-8N inhibitors potentially interfering with pathological lymphangiogenesis, autophagy, and tumor progression.

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.