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

Base Information

• Chemical Name: 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-β-D-glucopyranosyl fluoride
• CAS No.: 1415663-36-3
• Molecular Formula: C₂₂H₂₆FNO₄
• Molecular Weight: 387.451
• Mol file: 1415663-36-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-β-D-glucopyranosyl fluoride 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:

2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranose → 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-β-D-glucopyranosyl fluoride (1415663-36-3) + 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl fluoride (1415663-29-4)

Guidance literature:

With diethylamino-sulfur trifluoride; In tetrahydrofuran; at -30 ℃; for 5h; Overall yield = 91 %; Overall yield = 146 mg; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.10.064

Reference yield:

C16H25NO4 → 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-β-D-glucopyranosyl fluoride (1415663-36-3) + 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl fluoride (1415663-29-4)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: hydrazinium monoacetate / N,N-dimethyl-formamide / 8 h / 50 °C / Inert atmosphere

4: diethylamino-sulfur trifluoride / tetrahydrofuran / 5 h / -30 °C / Inert atmosphere

With pyridine; diethylamino-sulfur trifluoride; sulfuric acid; hydrazinium monoacetate; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2012.10.064

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-β-D-glucopyranosyl fluoride (1415663-36-3) + 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl fluoride (1415663-29-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 55 °C / Inert atmosphere

2.1: pyridine / dichloromethane / 3 h / 20 - 60 °C / Inert atmosphere

3.1: borane-THF / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

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

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

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

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

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

9.1: water / 6 h / Inert atmosphere; Heating

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

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

12.1: hydrazinium monoacetate / N,N-dimethyl-formamide / 8 h / 50 °C / Inert atmosphere

13.1: diethylamino-sulfur trifluoride / tetrahydrofuran / 5 h / -30 °C / Inert atmosphere

With pyridine; dmap; borane-THF; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; diethylamino-sulfur trifluoride; sulfuric acid; tri-n-butyl-tin hydride; sodium methylate; hydrazinium monoacetate; toluene-4-sulfonic acid; acetic acid; p-toluenesulfonyl chloride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2012.10.064

upstream raw materials:

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

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