2,3,4,6-Tetraacetyl-D-glucose

Base Information

• Chemical Name: 2,3,4,6-Tetraacetyl-D-glucose
• CAS No.: 10343-06-3
• Molecular Formula: C₁₄H₂₀O₁₀
• Molecular Weight: 348.307
• Hs Code.: 2940000080
• Mol file: 10343-06-3.mol

Synonyms:Glucopyranose,2,3,4,6-tetraacetate, D- (8CI);2,3,4,6-Tetra-O-acetyl-D-glucopyranose;

Chemical Property of 2,3,4,6-Tetraacetyl-D-glucose

Chemical Property:

• Vapor Pressure: 5.29E-09mmHg at 25°C
• Melting Point: 118-120°C
• Refractive Index: 1.491
• Boiling Point: 424.964 °C at 760 mmHg
• PKA: 11.44±0.70(Predicted)
• Flash Point: 148.473 °C
• PSA: 134.66000
• Density: 1.339 g/cm³
• LogP: -0.93820
• Storage Temp.: Refrigerator
• Solubility.: Soluble in chloroform or ethyl acetate

Purity/Quality:

99% ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-D-glucopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,3,4,6-Tetra-O-acetyl-D-glucopyranose (cas# 10343-06-3) is a compound useful in organic synthesis.

Technology Process of 2,3,4,6-Tetraacetyl-D-glucose

There total 259 articles about 2,3,4,6-Tetraacetyl-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: 100.0%

β-D-glucose pentaacetate (604-69-3) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3)

Guidance literature:

With hydrazinium monoacetate; In N,N-dimethyl-formamide; at 55 ℃; for 0.25h;

DOI:10.1016/S0040-4039(99)01558-0

Reference yield: 100.0%

D-Glucose (2280-44-6) + acetic anhydride (108-24-7) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3)

Guidance literature:

With pyridine; dmap; at 0 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201701620

Reference yield: 99.0%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3)

Guidance literature:

With water; silver carbonate; In acetone; for 0.5h;

DOI:10.1016/0008-6215(92)80015-S

upstream raw materials:

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

acetobromomannose

D-Mannose pentaacetate

D-Mannose

Downstream raw materials:

6-<4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl>-5,6-dihydro-2H-pyran-2-on

6-<4-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyloxy)phenyl>-5,6-dihydro-2H-pyran-2-on

Acetic acid (2R,3aR,5R,6R,7S,7aR)-6-acetoxy-5-acetoxymethyl-2-(4-methoxy-phenoxy)-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

Refernces

• 1、 Miyagawa, Atsushi,Kasuya, Maria Carmelita Z.,Hatanaka, Kenichi. "Immobilization of glycoconjugate polymers on cellulose membrane for affinity separation". . p. 348 - 356. Retrieved 2006.
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• 7、 Zhu, Zhenyuan,Li, Shengfeng,Liu, Rongqiang,Yuan, Jing,Wang, Haibiao,Zhang, Yongmin,Liu, Yang. "Regio- and stereo-selective synthesis of peracetylated carbohydrate esters of aromatic fatty acid using p-toluenesulfonic acid as catalyst". . p. 2245 - 2248. Retrieved 2010.
• 8、 Johnsson, Richard,Ellervik, Ulf. "Selective 1-O-deacetylation of carbohydrates using polymer-bound benzylamine". . p. 2939 - 2940. Retrieved 2005.
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• 10、 Lutteroth, Katherine R.,Harris, Paul W.R.,Wright, Tom H.,Kaur, Harveen,Sparrow, Kevin,Yang, Sung-Hyun,Cooper, Garth J.S.,Brimble, Margaret A.. "Incorporation of 'click' chemistry glycomimetics dramatically alters triple-helix stability in an adiponectin model peptide". . p. 5602 - 5608. Retrieved 2017.