1-O-acetyl-2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranose

Base Information

Chemical Name:1-O-acetyl-2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranose
CAS No.:1415663-22-7
Molecular Formula:C₂₄H₂₉NO₆
Molecular Weight:427.497
Hs Code.:

Synonyms:1-O-acetyl-2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranose

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Chemical Property of 1-O-acetyl-2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranose

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Technology Process of 1-O-acetyl-2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranose

There total 9 articles about 1-O-acetyl-2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranose 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: 67.0%

: 1415663-21-6
methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside

: 108-24-7
acetic anhydride

: 1415663-22-7
1-O-acetyl-2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranose

Guidance literature:: With sulfuric acid; acetic acid; for 48h; Inert atmosphere;
DOI:10.1016/j.bmcl.2012.10.064

Reference yield:

: 131589-93-0
methyl 2,3-di-O-benzoyl-4-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside

: 1415663-22-7
1-O-acetyl-2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranose

Guidance literature:: Multi-step reaction with 7 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

7: acetic acid; sulfuric acid / 48 h / Inert atmosphere

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; sodium methylate; acetic acid; p-toluenesulfonyl chloride; In methanol; dichloromethane; water; toluene;
DOI:10.1016/j.bmcl.2012.10.064

Reference yield:

: 89539-31-1
methyl 2,3-di-O-benzoyl-4-O-benzyl-α-D-glucopyranoside

: 1415663-22-7
1-O-acetyl-2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranose

Guidance literature:: Multi-step reaction with 8 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

8: acetic acid; sulfuric acid / 48 h / Inert atmosphere

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; sulfuric acid; tri-n-butyl-tin hydride; sodium methylate; acetic acid; p-toluenesulfonyl chloride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1016/j.bmcl.2012.10.064