Benzyl 2,3,4,6-Tetra-O-acetyl-beta-D-Glucopyranoside

Base Information

• Chemical Name: Benzyl 2,3,4,6-Tetra-O-acetyl-beta-D-Glucopyranoside
• CAS No.: 10343-13-2
• Molecular Formula: C₂₁H₂₆O₁₀
• Molecular Weight: 438.431
• Hs Code.: 2938909090
• DSSTox Substance ID: DTXSID70369550
• Nikkaji Number: J81.494F
• Wikidata: Q72497755
• Mol file: 10343-13-2.mol

Synonyms:10343-13-2;Benzyl 2,3,4,6-Tetra-O-acetyl-beta-D-Glucopyranoside;[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-phenylmethoxyoxan-2-yl]methyl acetate;(2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(benzyloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate;Benzyl 2,3,4,6-Tetra-O-acetyl-ss-D-Glucopyranoside;[(2R,3R,4S,5R,6R)-3,4,5-TRIS(ACETYLOXY)-6-(BENZYLOXY)OXAN-2-YL]METHYL ACETATE;Benzyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside;SCHEMBL15514610;DTXSID70369550;CCG-49702;AKOS004903160;AS-68140;Benzyl beta-D-glucopyranoside tetraacetate;CS-0440055;SR-01000639142-1;W-200698;Benzyl 2,3,4,6-Tetra-O-acetyl- beta -D-Glucopyranoside

Chemical Property of Benzyl 2,3,4,6-Tetra-O-acetyl-beta-D-Glucopyranoside

Chemical Property:

• Melting Point: 92-94°C
• Boiling Point: 499℃
• Flash Point: 214℃
• PSA: 123.66000
• Density: 1.27
• LogP: 1.28630
• Storage Temp.: Refrigerator
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 438.15259702
• Heavy Atom Count: 31
• Complexity: 642

Purity/Quality:

98%,99%, ^*data from raw suppliers

Benzyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside ^*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)OCC2=CC=CC=C2)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)OCC2=CC=CC=C2)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of Benzyl 2,3,4,6-Tetra-O-acetyl-beta-D-Glucopyranoside

There total 74 articles about Benzyl 2,3,4,6-Tetra-O-acetyl-beta-D-Glucopyranoside 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: 99.0%

tributylstannyl benzyl ether (33868-53-0) + tetra-O-acetyl-α-iodogalactopyranose (75801-94-4) → benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (10343-13-2,30657-70-6,31281-76-2,53729-76-3,142696-63-7,83113-54-6)

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1039/b809570a

Reference yield: 94.0%

benzyl alcohol (100-51-6,185532-71-2) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (10343-13-2,30657-70-6,31281-76-2,53729-76-3,83113-54-6,142696-63-7)

Guidance literature:

benzyl alcohol; With silver carbonate; In dichloromethane; for 2h; Molecular sieve; Darkness; Reflux;

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide; In dichloromethane; for 24h; Darkness; Reflux;

Reference yield: 90.8%

D-Mannose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) + benzyl alcohol (100-51-6,185532-71-2) → O-benzyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (10343-13-2,30657-70-6,31281-76-2,83113-54-6,142696-63-7,53729-76-3)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere; Molecular sieve;

DOI:10.1002/ejoc.200801024

upstream raw materials:

benzyl alcohol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

benzyl D-glucopyranoside

acetic anhydride

Downstream raw materials:

benzyl 2,3,4,6-tetra-O-benzyl-β-D-gluco-pyranoside

2,3,4,5-tetra-O-acetyl-D-glucopyranose

(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

O-benzyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Refernces

• 1、 Straubinger, Markus,Knapp, Holger,Oka, Noriaki,Watanabe, Naoharu,Winterhalter, Peter. "Isolation of a Glucosidic β-Damascenone Precursor from Rose Petals". . p. 4053 - 4056. Retrieved 1997.
• 2、 Matovi?, Jelena,J?rvinen, Juulia,Sokka, Iris K.,Imlimthan, Surachet,Raitanen, Jan-Erik,Montaser, Ahmed,Maaheimo, Hannu,Huttunen, Kristiina M.,Per?niemi, Sirpa,Airaksinen, Anu J.,Sarparanta, Mirkka,Johansson, Mikael P.,Rautio, Jarkko,Ekholm, Filip S.. "Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates". . p. 285 - 304. Retrieved 2021.
• 3、 Coen, Matthias,Engel, Ralf,Nahrstedt, Adolf. "Chavicol β-D-glucoside, a phenylpropanoid heteroside, benzyl-β-D-glucoside and glycosidically bound volatiles from subspecies of Cedronella canariensis". . p. 149 - 156. Retrieved 1995.
• 4、 Pakulski, Zbigniew. "Glycosylation in ionic liquids". . p. 2074 - 2078. Retrieved 2003.
• 5、 -. "INHIBITORS OF MALARIAL AND PLASMODIUM FALCIPARUM HEXOSE TRANSPORTER AND USES THEREOF". Paragraph 00513. . Retrieved 2021/08/14.