2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: 2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 229954-87-4
• Molecular Formula: C₄₅H₅₅NO₁₅Si
• Molecular Weight: 878.015
• Mol file: 229954-87-4.mol

Synonyms:2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of 2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-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-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 8 articles about 2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-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: 79.0%

2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (229954-86-3) → 2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (229954-87-4)

Guidance literature:

With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 2h; pH=3;

DOI:10.1016/S0008-6215(99)00018-X

Reference yield:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → 2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (229954-87-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / TsOH / acetonitrile / 2 h

2: BH₃NMe₃, AlCl₃ / tetrahydrofuran / 1 h / 60 °C

3: pyridine / 20 h

4: 1.) AgOTf, 2.) MeSBr / 1.) CH₂Cl₂, -70 deg C, 5 min, 2.) CH₂Cl₂, 1,2-dichloroethane, -70 deg C, 1 h

With aluminium trichloride; methanesulfonyl bromide; trimethylamine-borane; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; acetonitrile;

DOI:10.1021/jo981203x

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (229954-87-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / TsOH / acetonitrile / 2 h

2: BH₃NMe₃, AlCl₃ / tetrahydrofuran / 1 h / 60 °C

3: pyridine / 20 h

4: 1.) AgOTf, 2.) MeSBr / 1.) CH₂Cl₂, -70 deg C, 5 min, 2.) CH₂Cl₂, 1,2-dichloroethane, -70 deg C, 1 h

With aluminium trichloride; methanesulfonyl bromide; trimethylamine-borane; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; acetonitrile;

DOI:10.1021/jo981203x

upstream raw materials:

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

phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside

2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate

2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside