2-O-Methyl-α-D-glucopyranose tetraacetate

Base Information

• Chemical Name: 2-O-Methyl-α-D-glucopyranose tetraacetate
• CAS No.: 14199-55-4
• Molecular Formula: C₁₅H₂₂O₁₀
• Molecular Weight: 362.334
• Mol file: 14199-55-4.mol

Synonyms:Acetic acid (2R,3R,4S,5R,6R)-4,6-diacetoxy-2-acetoxymethyl-5-methoxy-tetrahydro-pyran-3-yl ester;Tetra-O-acetyl-2-O-methyl-α-D-glucopyranose;

Chemical Property of 2-O-Methyl-α-D-glucopyranose tetraacetate

Chemical Property:

• PSA: 123.66000
• LogP: -0.28410

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-Methyl-α-D-glucopyranose tetraacetate

There total 9 articles about 2-O-Methyl-α-D-glucopyranose tetraacetate 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: 81.0%

methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-mannopyranoside (65877-23-8) + acetic anhydride (108-24-7) → 1,3,4,6-tetra-O-acetyl-2-O-methyl-α-D-mannopyranose (7226-48-4,10357-30-9,14199-54-3,14199-55-4,14199-57-6,18968-06-4,32445-64-0,32475-75-5,52645-74-6,67322-02-5,100018-31-3,101540-16-3,140148-47-6)

Guidance literature:

With sulfuric acid; acetic acid; at 20 ℃; Inert atmosphere;

DOI:10.3762/bjoc.8.136

Reference yield: 47.0%

D-Galactose (10257-28-0) + acetic anhydride (108-24-7) → 1,2,3,4,6-penta-O-acetyl-β-D-galactopyranoside (7226-48-4,10357-30-9,14199-54-3,14199-55-4,14199-57-6,18968-06-4,32445-64-0,32475-75-5,52645-74-6,67322-02-5,100018-31-3,101540-16-3,140148-47-6)

Guidance literature:

With sodium acetate; at 100 ℃; for 2.25h; optical yield given as %de; air;

DOI:10.1002/ejoc.201200277

Reference yield:

methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-mannopyranoside (64605-18-1) → 1,3,4,6-tetra-O-acetyl-2-O-methyl-α-D-mannopyranose (7226-48-4,10357-30-9,14199-54-3,14199-55-4,14199-57-6,18968-06-4,32445-64-0,32475-75-5,52645-74-6,67322-02-5,100018-31-3,101540-16-3,140148-47-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂; aq. HCl / Pd/C / ethanol / 18 h / 3800 Torr

2: 1.55 g / AcOH; H₂SO₄

With hydrogenchloride; sulfuric acid; hydrogen; acetic acid; palladium on activated charcoal; In ethanol; 1: Hydrogenolysis / 2: Acetylation;

DOI:10.1080/07328300008544084

upstream raw materials:

methyl 2-O-methyl-α-D-mannopyranoside

acetic anhydride

methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-mannopyranoside

methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-mannopyranoside

Downstream raw materials:

2-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyloxy)acetaldehyde

(2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside

(2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside

4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-threo-hex-1-en-3-ulose

Refernces

• 1、 Zou, Lu,Zheng, Ruixiang Blake,Lowary, Todd L.. "Studies on the substrate specificity of a GDP-mannose pyrophosphorylase from Salmonella enterica". supporting information; experimental part. p. 1219 - 1226. Retrieved 2012/09/21.
• 2、 Hakamata, Wataru,Nishio, Toshiyuki,Sato, Reiko,Mochizuki, Takahiro,Tsuchiya, Kazuya,Yasuda, Maki,Oku, Tadatake. "Synthesis of monomethyl derivatives of p-nitrophenyl α-d-gluco, galacto, and mannopyranosides and their hydrolytic properties against α-glycosidases". . p. 359 - 377. Retrieved 2007/10/03.