methyl 4-O-benzyl-7-deoxy-2,3-di-O-methyl-8-O-p-toluenesulfonyl-β-L-glycero-D-galactooctopyranoside

Base Information

• Chemical Name: methyl 4-O-benzyl-7-deoxy-2,3-di-O-methyl-8-O-p-toluenesulfonyl-β-L-glycero-D-galactooctopyranoside
• CAS No.: 1454689-64-5
• Molecular Formula: C₂₆H₃₆O₉S
• Molecular Weight: 524.632
• Mol file: 1454689-64-5.mol

Synonyms:methyl 4-O-benzyl-7-deoxy-2,3-di-O-methyl-8-O-p-toluenesulfonyl-β-L-glycero-D-galactooctopyranoside

Chemical Property of methyl 4-O-benzyl-7-deoxy-2,3-di-O-methyl-8-O-p-toluenesulfonyl-β-L-glycero-D-galactooctopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-benzyl-7-deoxy-2,3-di-O-methyl-8-O-p-toluenesulfonyl-β-L-glycero-D-galactooctopyranoside

There total 7 articles about methyl 4-O-benzyl-7-deoxy-2,3-di-O-methyl-8-O-p-toluenesulfonyl-β-L-glycero-D-galactooctopyranoside 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: 92.0%

methyl 4-O-benzyl-7-deoxy-2,3-di-O-methyl-β-L-glycero-D-galactooctopyranoside (1454689-61-2) + p-toluenesulfonyl chloride (98-59-9) → methyl 4-O-benzyl-7-deoxy-2,3-di-O-methyl-8-O-p-toluenesulfonyl-β-L-glycero-D-galactooctopyranoside (1454689-64-5)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; In acetonitrile; at 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1021/ja405588x

Reference yield:

(6S)-methyl 6-C-allyl-4-O-benzyl-2,3-di-O-methyl-α-D-galactopyranoside (1454689-57-6) → methyl 4-O-benzyl-7-deoxy-2,3-di-O-methyl-8-O-p-toluenesulfonyl-β-L-glycero-D-galactooctopyranoside (1454689-64-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 5 h / 0 - 20 °C / Inert atmosphere

2.1: ozone; oxygen / dichloromethane; methanol / -70 °C / Inert atmosphere

2.2: 10 h / -70 - 20 °C / Inert atmosphere

3.1: N,N,N,N,-tetramethylethylenediamine / acetonitrile / 2.5 h / 20 °C / Inert atmosphere

With N,N,N,N,-tetramethylethylenediamine; oxygen; sodium hydride; ozone; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1021/ja405588x

Reference yield:

methyl 4,6-O-benzylidene-α-D-galactopyranoside (64552-06-3) → methyl 4-O-benzyl-7-deoxy-2,3-di-O-methyl-8-O-p-toluenesulfonyl-β-L-glycero-D-galactooctopyranoside (1454689-64-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / Inert atmosphere

2.1: borane-THF / dichloromethane / 0.75 h / 20 °C / Inert atmosphere

2.2: 5 h / 20 °C / Inert atmosphere

3.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 2.5 h / -78 °C / Inert atmosphere

3.2: 3 h / -78 - 20 °C / Inert atmosphere

4.1: tetrahydrofuran; diethyl ether / 5 h / -30 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

5.2: 5 h / 0 - 20 °C / Inert atmosphere

6.1: ozone; oxygen / dichloromethane; methanol / -70 °C / Inert atmosphere

6.2: 10 h / -70 - 20 °C / Inert atmosphere

7.1: N,N,N,N,-tetramethylethylenediamine / acetonitrile / 2.5 h / 20 °C / Inert atmosphere

With borane-THF; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; oxygen; sodium hydride; ozone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; mineral oil; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;

DOI:10.1021/ja405588x

upstream raw materials:

methyl 4,6-O-benzylidene-α-D-galactopyranoside

methyl 4-O-benzyl-2,3-di-O-methyl-α-D-galactopyranoside

(6S)-methyl 6-C-allyl-4-O-benzyl-2,3-di-O-methyl-α-D-galactopyranoside

methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-galactopyranoside

Downstream raw materials:

methyl 7-deoxy-2,3-di-O-methyl-8-O-p-toluenesulfonyl-β-L-glycero-D-galactooctopyranoside

Refernces