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

Base Information

• Chemical Name: 2-((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(thiazol-2-yl)-tetrahydro-2H-pyran-2-yl)thiazole
• CAS No.: 154172-46-0
• Molecular Formula: C₃₇H₃₇NO₅S
• Molecular Weight: 607.77
• Mol file: 154172-46-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 2-((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(thiazol-2-yl)-tetrahydro-2H-pyran-2-yl)thiazole 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:

1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-(2-thiazolyl)-α-D-glucopyranose (154127-56-7) → 2-((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(thiazol-2-yl)-tetrahydro-2H-pyran-2-yl)thiazole (154127-57-8) + 2-((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(thiazol-2-yl)-tetrahydro-2H-pyran-2-yl)thiazole (154172-46-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; Dimethylphenylsilane; In dichloromethane; for 0.25h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4039(00)79319-1

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → 2-((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(thiazol-2-yl)-tetrahydro-2H-pyran-2-yl)thiazole (154172-46-0)

Guidance literature:

Multi-step reaction with 3 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

3: 4-Angstroem molecular sieves, Et₃SiH, TMSOTf / CH₂Cl₂ / 0.5 h / Ambient temperature

With triethylsilane; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 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) → 2-((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(thiazol-2-yl)-tetrahydro-2H-pyran-2-yl)thiazole (154172-46-0)

Guidance literature:

Multi-step reaction with 4 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

4: 4-Angstroem molecular sieves, Et₃SiH, TMSOTf / CH₂Cl₂ / 0.5 h / Ambient temperature

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

DOI:10.1021/jo00100a050

upstream raw materials:

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

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

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

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Downstream raw materials:

2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose