ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Base Information

• Chemical Name: ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• CAS No.: 79218-68-1
• Molecular Formula: C₂₉H₃₂O₇
• Molecular Weight: 492.569
• Mol file: 79218-68-1.mol

Synonyms:ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Chemical Property of ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

There total 49 articles about ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 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: 98.0%

acetic anhydride (108-24-7) + 3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose (68681-00-5) → ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside (79218-68-1)

Guidance literature:

3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose; With acetic acid; In water; at 20 ℃; for 4h; Inert atmosphere;

acetic anhydride; With pyridine; at 0 - 20 ℃; for 16h; Inert atmosphere;

With benzylamine; In tetrahydrofuran; at 20 ℃; for 22h; Inert atmosphere;

DOI:10.1021/ja4056678

Reference yield: 95.0%

3,4,6-tri-O-benzyl-1,2-O-(1-ethoxyethylidene)-α-D-galactopyranose (66492-24-8) → 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranose (79218-68-1,88988-46-9,93495-88-6,108869-76-7,127875-27-8,127875-34-7,129214-38-6,148968-88-1)

Guidance literature:

With acetic acid; In pyridine; at 22 ℃; for 24h;

DOI:10.1002/hlca.19940770211

Reference yield: 90.0%

1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside (65827-55-6,68567-54-4,77790-45-5,77790-46-6,81969-44-0,99630-89-4,125135-30-0,137567-77-2,55628-56-3) → 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose (79218-68-1,88988-46-9,93495-88-6,108869-76-7,127875-27-8,127875-34-7,129214-38-6,148968-88-1)

Guidance literature:

With hydrazinium monoacetate; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h;

DOI:10.1002/chem.200390025

upstream raw materials:

3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose

1,2-O-(1-ethoxyethylene) 3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranose

benzyl bromide

benzyl chloride

Downstream raw materials:

methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl-2,3,4-tri-O-benzyl-6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside

benzyl 6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

benzyl 6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Refernces

• 1、 Wawryszyn, Mirella,Sauter, Paul F.,Nieger, Martin,Koos, Martin R. M.,Koehler, Christine,Luy, Burkhard,Lemke, Edward A.,Br?se, Stefan. "Synthesis of Azido-Glycans for Chemical Glycomodification of Proteins". supporting information. p. 4296 - 4305. Retrieved 2018/08/29.
• 2、 Cancogni, Damiano,Lay, Luigi. "Exploring glycosylation reactions under continuous-flow conditions". supporting information. p. 2873 - 2878. Retrieved 2015/01/16.