benzyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-pivaloyl-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-pivaloyl-β-D-glucopyranoside
• CAS No.: 158420-81-6
• Molecular Formula: C₃₃H₃₅NO₈
• Molecular Weight: 573.643
• Mol file: 158420-81-6.mol

Synonyms:benzyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-pivaloyl-β-D-glucopyranoside

Chemical Property of benzyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-pivaloyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-pivaloyl-β-D-glucopyranoside

There total 6 articles about benzyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-pivaloyl-β-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: 86.0%

pivaloyl chloride (3282-30-2) + benzyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (80035-35-4) → benzyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-pivaloyl-β-D-glucopyranoside (158420-81-6)

Guidance literature:

In pyridine; at 0 ℃; for 4h;

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → benzyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-pivaloyl-β-D-glucopyranoside (158420-81-6)

Guidance literature:

Multi-step reaction with 6 steps

2: 92 percent / conc. HCl / acetone / 70 °C

3: 82 percent / TsOH / dimethylformamide / 50 °C

4: 1.) NaH / 1.) DMF, room temperature, 30 min, 2.) room temperature, 5 h

5: 90 percent / aq. AcOH / 1.5 h / 70 °C

6: 86 percent / pyridine / 4 h / 0 °C

With hydrogenchloride; sodium hydride; toluene-4-sulfonic acid; acetic acid; In pyridine; N,N-dimethyl-formamide; acetone;

Reference yield:

benzyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (80035-32-1) → benzyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-pivaloyl-β-D-glucopyranoside (158420-81-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / TsOH / dimethylformamide / 50 °C

2: 1.) NaH / 1.) DMF, room temperature, 30 min, 2.) room temperature, 5 h

3: 90 percent / aq. AcOH / 1.5 h / 70 °C

4: 86 percent / pyridine / 4 h / 0 °C

With sodium hydride; toluene-4-sulfonic acid; acetic acid; In pyridine; N,N-dimethyl-formamide;

upstream raw materials:

pivaloyl chloride

benzyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

benzyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

benzyl 3-O-benzyl-2-deoxy-4-O-(3',6'-di-O-benzyl-4'-O-chloroacetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-2-phthalimido-6-O-pivaloyl-β-D-glucopyranoside

benzyl 3-O-benzyl-2-deoxy-4-O-(3',6'-di-O-benzyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-2-phthalimido-6-O-pivaloyl-β-D-glucopyranoside