1-O-acetyl-2,3,4-tri-O-benzyl-1-C-(2-benzothiazolyl)-α-L-fucopyranose

Base Information

• Chemical Name: 1-O-acetyl-2,3,4-tri-O-benzyl-1-C-(2-benzothiazolyl)-α-L-fucopyranose
• CAS No.: 869500-64-1
• Molecular Formula: C₃₆H₃₅NO₆S
• Molecular Weight: 609.743
• Mol file: 869500-64-1.mol

Synonyms:1-O-acetyl-2,3,4-tri-O-benzyl-1-C-(2-benzothiazolyl)-α-L-fucopyranose

Chemical Property of 1-O-acetyl-2,3,4-tri-O-benzyl-1-C-(2-benzothiazolyl)-α-L-fucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-acetyl-2,3,4-tri-O-benzyl-1-C-(2-benzothiazolyl)-α-L-fucopyranose

There total 3 articles about 1-O-acetyl-2,3,4-tri-O-benzyl-1-C-(2-benzothiazolyl)-α-L-fucopyranose 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:

(2S,3S,4R,5R,6S)-2-Benzothiazol-2-yl-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ol (869500-63-0) + acetic anhydride (108-24-7) → 1-O-acetyl-2,3,4-tri-O-benzyl-1-C-(2-benzothiazolyl)-α-L-fucopyranose (869500-64-1)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1021/jo051377w

Reference yield:

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol (162118-38-9) → 1-O-acetyl-2,3,4-tri-O-benzyl-1-C-(2-benzothiazolyl)-α-L-fucopyranose (869500-64-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridinium chlorochromate

2.1: n-butyllithium / diethyl ether; hexane / 0.75 h / -70 °C

2.2: diethyl ether; hexane / 2.25 h / -70 - -50 °C

3.1: 1.02 g / triethylamine / CH₂Cl₂ / 48 h / 20 °C

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

DOI:10.1021/jo051377w

Reference yield:

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one (144668-21-3) → 1-O-acetyl-2,3,4-tri-O-benzyl-1-C-(2-benzothiazolyl)-α-L-fucopyranose (869500-64-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / diethyl ether; hexane / 0.75 h / -70 °C

1.2: diethyl ether; hexane / 2.25 h / -70 - -50 °C

2.1: 1.02 g / triethylamine / CH₂Cl₂ / 48 h / 20 °C

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

DOI:10.1021/jo051377w

upstream raw materials:

(2S,3S,4R,5R,6S)-2-Benzothiazol-2-yl-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ol

acetic anhydride

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

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

Downstream raw materials:

2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-phenyl-aldehydo-L-glycero-D-manno-heptose

2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-(2-thiazolyl)-aldehydo-L-glycero-D-manno-heptose

3-Methyl-2-phenyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dihydro-benzothiazole

3-Methyl-2-thiazol-2-yl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dihydro-benzothiazole