phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside

Base Information

• Chemical Name: phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside
• CAS No.: 850647-86-8
• Molecular Formula: C₃₄H₃₆O₆S
• Molecular Weight: 572.722
• Mol file: 850647-86-8.mol

Synonyms:phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside

Chemical Property of phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside

There total 4 articles about phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside 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: 90.0%

phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside (808762-01-8) → phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside (850647-86-8)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 - 0 ℃; for 5h;

DOI:10.1021/ol050224s DOI:10.1021/ja061594u

Reference yield:

phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside (449761-78-8) → phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside (850647-86-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / Inert atmosphere; Cooling

3: tetrabutyl ammonium fluoride / dichloromethane; tetrahydrofuran / 18 h / Inert atmosphere

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jo302455d

Reference yield:

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside → phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside (850647-86-8)

Guidance literature:

Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid / dichloromethane; methanol / 18 h / 20 °C / Inert atmosphere

2: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere

3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / Inert atmosphere; Cooling

4: tetrabutyl ammonium fluoride / dichloromethane; tetrahydrofuran / 18 h / Inert atmosphere

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jo302455d

upstream raw materials:

phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside

phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside

phenylthio 2,3-di-O-benzyl-6-(tert-butyldimethylsiloxy)-α-D-mannopyranoside

Downstream raw materials:

phenylthio 2,3-di-O-benzyl-6,7-dideoxy-8-C-phenyl-α-D-manno-oct-8-ulopyranoside

phenylthio 2,3-di-O-benzyl-6,7-dideoxy-8-C-phenyl-4-O-(trimethylsilyl)-α-D-manno-oct-8-ulopyranoside

phenylthio 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8-methoxy-8S-C-phenyl-α-D-manno-octopyranoside

(Z)-phenylthio 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8-C-phenyl-α-D-manno-oct-7-enopyranoside