2-(trimethylsilyl)ethyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 281658-12-6
• Molecular Formula: C₃₃H₃₉NO₇Si
• Molecular Weight: 589.761
• Mol file: 281658-12-6.mol

Synonyms:2-(trimethylsilyl)ethyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 5 articles about 2-(trimethylsilyl)ethyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-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: 54.0%

2-(trimethylsilyl)ethyl 3-O-allyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (281658-11-5) → 2-(trimethylsilyl)ethyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (281658-12-6)

Guidance literature:

With palladium dichloride; In methanol; at 25 ℃; for 4h;

DOI:10.1016/S0008-6215(00)00011-2

Reference yield:

benzyl bromide (100-39-0) → 2-(trimethylsilyl)ethyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (281658-12-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / NaH / dimethylformamide

2: 54 percent / PdCl₂ / methanol / 4 h / 25 °C

With sodium hydride; palladium dichloride; In methanol; N,N-dimethyl-formamide; 1: benzylation / 2: ether cleavage;

DOI:10.1016/S0008-6215(00)00011-2

Reference yield:

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (174392-90-6) → 2-(trimethylsilyl)ethyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (281658-12-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH (60 percent iol coated) / dimethylformamide / 0.5 h / 0 °C

1.2: 29 percent / dimethylformamide / 7 h / 20 °C

2.1: 95 percent / AcOH / H₂O / 2 h / 80 °C

3.1: 55 percent / NaH / dimethylformamide

4.1: 54 percent / PdCl₂ / methanol / 4 h / 25 °C

With sodium hydride; acetic acid; palladium dichloride; In methanol; water; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: allylation / 2.1: Hydrolysis / 3.1: benzylation / 4.1: ether cleavage;

DOI:10.1016/S0008-6215(00)00011-2

upstream raw materials:

2-(trimethylsilyl)ethyl 3-O-allyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

benzyl bromide

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

2-(trimethylsilyl)ethyl 3-O-allyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

2-(trimethylsilyl)ethyl 2-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

2-(trimethylsilyl)ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside