Acetochloro-beta-D-glucose

Base Information

• Chemical Name: Acetochloro-beta-D-glucose
• CAS No.: 4451-36-9
• Molecular Formula: C14H19 Cl O9
• Molecular Weight: 366.752
• European Community (EC) Number: 674-530-1
• DSSTox Substance ID: DTXSID70449861
• Nikkaji Number: J322.175J
• Wikidata: Q76416322
• Mol file: 4451-36-9.mol

Synonyms:4451-36-9;Acetochloro-beta-D-glucose;(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-chlorotetrahydro-2H-pyran-3,4,5-triyl triacetate;2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl chloride;[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-chlorooxan-2-yl]methyl acetate;(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-chloro-tetrahydro-2H-pyran-3,4,5-triyl triacetate;ss-Acetochloro-D-glucose;SCHEMBL11391303;DTXSID70449861;BYWPSIUIJNAJDV-RKQHYHRCSA-N;GEO-00008;(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-chlorotetrahydro-2H-pyran-3,4,5-triyltriacetate;tetra-O-acetyl-beta-d-glucopyranosyl chloride;I(2)-D-Glucopyranosyl chloride, tetraacetate;.beta.-D-Glucopyranosyl chloride, tetraacetate;Glucopyranosyl chloride, tetraacetate, .beta.-D-;1-Chloro-1-deoxy-beta-D-glucopyranose tetraacetate;W-200378

Chemical Property of Acetochloro-beta-D-glucose

Chemical Property:

• Vapor Pressure: 1.36E-10mmHg at 25°C
• Melting Point: 98-99 °C(Solv: ethyl ether (60-29-7))
• Refractive Index: 1.504
• Boiling Point: 481.4°C at 760 mmHg
• Flash Point: 245°C
• PSA: 114.43000
• Density: 1.44g/cm³
• LogP: 0.30830
• 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:

99%min ^*data from raw suppliers

(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-chloro-tetrahydro-2H-pyran-3,4,5-triyl triacetate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)Cl)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of Acetochloro-beta-D-glucose

There total 44 articles about Acetochloro-beta-D-glucose 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: 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

Reference yield: 91.0%

β-D-glucose pentaacetate (604-69-3) → 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride (4451-36-9)

Guidance literature:

With thionyl chloride; acetic acid; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1016/0008-6215(93)80045-G

Reference yield: 75.0%

C20H23NO11 → 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride (4451-36-9)

Guidance literature:

With copper dichloride; In dichloromethane; at 20 ℃; Molecular sieve; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00078

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:

(1S)-1-(4-methoxy-phenyl)-1,5-anhydro-D-mannitol

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

methyl-(tetra-O-acetyl-glucopyranoside)

p-tolyl-glucopyranoside

Refernces

• 1、 Kim,Kinghorn,Kim. "Semisynthesis of abrusoside A methyl ester.". . p. 223 - 224. Retrieved 1999.
• 2、 Balzer, Paul G.,Blaszczyk, Stephanie A.,Duan, Xiyan,Ma, Zhi-Xiong,Simmons, Christopher J.,Stevens, Christopher M.,Tang, Weiping,Wang, Hao-Yuan,Wen, Peng,Ye, Wenjing,Yin, Dan. "Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions". supporting information. . Retrieved 2020/02/28.
• 3、 Bütikofer, Peter,H?ner, Robert,Khorev, Oleg,Langenegger, Simon M.,Menon, Anant K.,Picca, Giovanni,Probst, Markus. "Nonenzymatic synthesis of anomerically pure, mannosylbased molecular probes for scramblase identification studies". supporting information. p. 1732 - 1739. Retrieved 2020/09/15.