2,3,4,6-tetra-O-acetyl-beta-D-chloroglucose

Base Information

• Chemical Name: 2,3,4,6-tetra-O-acetyl-beta-D-chloroglucose
• CAS No.: 14257-40-0
• Molecular Formula: C₁₄H₁₉ClO₉
• Molecular Weight: 366.752
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID00931527
• Mol file: 14257-40-0.mol

Synonyms:2,3,4,6-tetra-O-acetyl-beta-D-chloroglucose;66966-08-3;(3,4,5-triacetyloxy-6-chlorooxan-2-yl)methyl acetate;.alpha.-D-Mannopyranosyl chloride, tetraacetate;Mannopyranosyl chloride, tetraacetate, .alpha.-D-;SCHEMBL19680965;SCHEMBL22852931;DTXSID00931527;(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-chloro-tetrahydro-2H-pyran-3,4,5-triyl triacetate;AKOS030212688;SY249848;FT-0623611;FT-0654095;FT-0674893;FT-0771851;2,3,4,6-Tetra-O-acetylhexopyranosyl chloride;2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYLCHLORIDE;4-Bis(4-methylphenyl)aminobenzo pound-aldehyde-1,1-diphenylhydrazone

Chemical Property of 2,3,4,6-tetra-O-acetyl-beta-D-chloroglucose

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 8.15E-07mmHg at 25°C
• Melting Point: 69-71 °C
• Refractive Index: 1.486
• Boiling Point: 406.4 °C at 760 mmHg
• Flash Point: 144.2 °C
• PSA: 114.43000
• Density: 1.33 g/cm³
• LogP: 0.30830
• Storage Temp.: Store below -20C
• Solubility.: Chloroform, Ether
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 366.0717599
• Heavy Atom Count: 24
• Complexity: 507

Purity/Quality:

98%Min ^*data from raw suppliers

6-Chloro-6-deoxy-D-mannose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)Cl)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: Chloro 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranoside is a mannose derivative. D-Mannose is a carbohydrate that is important in the glycosylation of molecules in a variety of cellular processes (1,2).

Technology Process of 2,3,4,6-tetra-O-acetyl-beta-D-chloroglucose

There total 24 articles about 2,3,4,6-tetra-O-acetyl-beta-D-chloroglucose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.2%

1,2,3,4,6-penta-O-acetyl-β-D-galactopyranoside → 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0)

Guidance literature:

With phosphorus pentachloride; boron trifluoride diethyl etherate; In dichloromethane; for 0.5h;

Reference yield: 94.0%

β-D-galactose peracetate (4163-60-4) → 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0)

Guidance literature:

With phosphorus pentachloride; boron trifluoride diethyl etherate; In dichloromethane; for 0.0833333h;

DOI:10.1016/S0040-4039(02)02446-2

Reference yield: 92.0%

2,3,4,6-tetra-O-acetyl-D-mannopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1) → 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; In 1,2-dichloro-ethane; at 60 ℃; for 2h;

DOI:10.1016/j.tetlet.2009.05.077

upstream raw materials:

β-D-mannopyranose pentaacetate

per-O-acetyl-α-D-mannopyranose

2,3,4,6-tetra-O-acetyl-D-mannopyranose

2-(Trimethylsilyl)ethyl-<2,3,4,6-tetra-O-acetyl-α-D-mannopyranosid>

Downstream raw materials:

2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl chloride

propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

Refernces

• 1、 Li, Zhihao,Bavaro, Teodora,Tengattini, Sara,Bernardini, Roberta,Mattei, Maurizio,Annunziata, Francesca,Cole, Richard B.,Zheng, Changping,Sollogoub, Matthieu,Tamborini, Lucia,Terreni, Marco,Zhang, Yongmin. "Chemoenzymatic synthesis of arabinomannan (AM) glycoconjugates as potential vaccines for tuberculosis". supporting information. . Retrieved 2020/07/27.
• 2、 Pongener, Imlirenla,Nikitin, Kirill,McGarrigle, Eoghan M.. "Synthesis of glycosyl chlorides using catalytic Appel conditions". supporting information. p. 7531 - 7535. Retrieved 2019/08/20.