methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside
• CAS No.: 1415663-21-6
• Molecular Formula: C₂₃H₂₉NO₅
• Molecular Weight: 399.487
• Mol file: 1415663-21-6.mol

Synonyms:methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside

Chemical Property of methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside

There total 10 articles about methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside 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:

C16H25NO4 + benzoyl chloride (98-88-4) → methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside (1415663-21-6)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.10.064

Reference yield:

methyl 2,3-di-O-benzoyl-4-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside (131589-93-0) → methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside (1415663-21-6)

Guidance literature:

Multi-step reaction with 6 steps

1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 3.5 h / 20 - 80 °C / Inert atmosphere

2: sodium methylate / dichloromethane; methanol / 10 h / pH 10

3: pyridine; p-toluenesulfonyl chloride; dmap / 20 - 80 °C / Inert atmosphere

4: sodium methylate / dichloromethane; methanol / 48 h / 0 - 5 °C / Inert atmosphere

5: water / 6 h / Inert atmosphere; Heating

6: pyridine / 3 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; p-toluenesulfonyl chloride; In methanol; dichloromethane; water; toluene;

DOI:10.1016/j.bmcl.2012.10.064

Reference yield:

methyl 2,3-di-O-benzoyl-4-O-benzyl-α-D-glucopyranoside (89539-31-1) → methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside (1415663-21-6)

Guidance literature:

Multi-step reaction with 7 steps

1: triphenylphosphine; carbon tetrabromide / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere

2: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 3.5 h / 20 - 80 °C / Inert atmosphere

3: sodium methylate / dichloromethane; methanol / 10 h / pH 10

4: pyridine; p-toluenesulfonyl chloride; dmap / 20 - 80 °C / Inert atmosphere

5: sodium methylate / dichloromethane; methanol / 48 h / 0 - 5 °C / Inert atmosphere

6: water / 6 h / Inert atmosphere; Heating

7: pyridine / 3 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tri-n-butyl-tin hydride; sodium methylate; p-toluenesulfonyl chloride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; toluene;

DOI:10.1016/j.bmcl.2012.10.064

upstream raw materials:

benzoyl chloride

benzaldehyde dimethyl acetal

methyl 2,3-di-O-benzoyl-4-O-benzyl-α-D-glucopyranoside

methyl 2,3-di-O-benzoyl-4-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside

Downstream raw materials:

2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-β-D-glucopyranosyl fluoride

2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl fluoride

p-methylphenyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside

ethyl 2-O-benzoyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside