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

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-galactopyranoside
• CAS No.: 229954-88-5
• Molecular Formula: C₄₇H₅₇NO₁₆Si
• Molecular Weight: 920.052
• Mol file: 229954-88-5.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-galactopyranoside

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-galactopyranoside

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-galactopyranoside

There total 5 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-galactopyranoside 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: 89.0%

tetramethyl ammonium acetate (10581-12-1) + acetic acid 4,5-diacetoxy-6-benzyloxymethyl-2-[2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-trifluoromethanesulfonyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester → 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 (229954-88-5)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 2h;

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

Reference yield:

ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside (107855-14-1) → 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 (229954-88-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / powdered 4 Angstroem molecular sieves; NIS; TfOH / CH₂Cl₂ / 1 h / -40 °C

2: 79 percent / powdered 3 Angstroem molecular sieves; sodium cyanoborohydride; HCl / tetrahydrofuran; diethyl ether / 2 h / 0 °C / pH 3

3: pyridine / CH₂Cl₂ / 4 h / 20 °C

4: 89 percent / dimethylformamide / 2 h / 20 °C

With pyridine; hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; 4 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Hydrolysis / 3: Esterification / 4: transesterification;

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

Reference yield:

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (174392-90-6) → 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 (229954-88-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / powdered 4 Angstroem molecular sieves; NIS; TfOH / CH₂Cl₂ / 1 h / -40 °C

2: 79 percent / powdered 3 Angstroem molecular sieves; sodium cyanoborohydride; HCl / tetrahydrofuran; diethyl ether / 2 h / 0 °C / pH 3

3: pyridine / CH₂Cl₂ / 4 h / 20 °C

4: 89 percent / dimethylformamide / 2 h / 20 °C

With pyridine; hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; 4 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Hydrolysis / 3: Esterification / 4: transesterification;

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

upstream raw materials:

tetramethyl ammonium acetate

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

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

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

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