1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-(2-thiazolyl)-α-D-glucopyranose

Base Information

• Chemical Name: 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-(2-thiazolyl)-α-D-glucopyranose
• CAS No.: 154127-56-7
• Molecular Formula: C₃₉H₃₉NO₇S
• Molecular Weight: 665.807
• Mol file: 154127-56-7.mol

Synonyms:1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-(2-thiazolyl)-α-D-glucopyranose

Chemical Property of 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-(2-thiazolyl)-α-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-(2-thiazolyl)-α-D-glucopyranose

There total 5 articles about 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-(2-thiazolyl)-α-D-glucopyranose 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%

acetic anhydride (108-24-7) + 2,3,4,6-tetra-O-benzyl-β-1-C-(2-thiazolyl)-D-glucopyranose (154127-55-6) → 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-(2-thiazolyl)-α-D-glucopyranose (154127-56-7)

Guidance literature:

With triethylamine; In dichloromethane; Ambient temperature;

DOI:10.1021/jo00100a050

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-(2-thiazolyl)-α-D-glucopyranose (154127-56-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / n-BuLi / hexane; diethyl ether / 1.) -78 deg C, 20 min, 2.) THF, -78 deg C, 20 min; -78 to -65 deg C, 30 min

2: 100 percent / Et₃N / CH₂Cl₂ / Ambient temperature

With n-butyllithium; triethylamine; In diethyl ether; hexane; dichloromethane;

DOI:10.1021/jo00100a050

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-(2-thiazolyl)-α-D-glucopyranose (154127-56-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 4-Angstroem molecular sieves, pyridinium chlorochromate

2: 80 percent / n-BuLi / hexane; diethyl ether / 1.) -78 deg C, 20 min, 2.) THF, -78 deg C, 20 min; -78 to -65 deg C, 30 min

3: 100 percent / Et₃N / CH₂Cl₂ / Ambient temperature

With n-butyllithium; 4 A molecular sieve; triethylamine; pyridinium chlorochromate; In diethyl ether; hexane; dichloromethane;

DOI:10.1021/jo00100a050

upstream raw materials:

acetic anhydride

2,3,4,6-tetra-O-benzyl-β-1-C-(2-thiazolyl)-D-glucopyranose

2-bromo-1,3-thiazole

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Downstream raw materials:

2-((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(thiazol-2-yl)-tetrahydro-2H-pyran-2-yl)thiazole

2-((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(thiazol-2-yl)-tetrahydro-2H-pyran-2-yl)thiazole

methyl 2,3,4-tri-O-benzyl-6-O-[2,3,4,6-tetra-O-benzyl-1-C-(2-thiazolyl)-β-D-glucopyranosyl]-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-[2,3,4,6-tetra-O-benzyl-1-C-(2-thiazolyl)-α-D-glucopyranosyl]-α-D-glucopyranoside