2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside
• CAS No.: 148852-74-8
• Molecular Formula: C₂₈H₄₀O₆Si
• Molecular Weight: 500.707
• Mol file: 148852-74-8.mol

Synonyms:2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside

There total 2 articles about 2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-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: 86.7%

benzyl bromide (100-39-0) + 2-(trimethylsilyl)ethyl 3,4-O-isopropylidene-β-D-galactopyranoside (123956-78-5) → 2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside (148852-74-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1081/CAR-120026456

Reference yield:

2-(trimethylsilyl)ethyl β-D-galactopyranoside (117252-95-6) → 2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside (148852-74-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 63.8 percent / 10-camphorsulfonic acid / dimethylformamide / 12 h / 20 °C

2: 86.7 percent / NaH / dimethylformamide / 3 h / 20 °C

With (1S)-10-camphorsulfonic acid; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1081/CAR-120026456

Reference yield: 93.0%

2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside (148852-74-8) → 2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-β-D-galactopyranoside (177280-23-8)

Guidance literature:

With acetic acid; at 60 ℃; for 6h;

DOI:10.1016/S0008-6215(98)00053-6

upstream raw materials:

benzyl bromide

2-(trimethylsilyl)ethyl 3,4-O-isopropylidene-β-D-galactopyranoside

2-(trimethylsilyl)ethyl β-D-galactopyranoside

Downstream raw materials:

2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-β-D-galactopyranoside

2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-3-O-(4-methoxybenzyl)-β-D-galactopyranoside

2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,6-di-O-benzyl-3-O-(4-methoxybenzyl)-β-D-galactopyranoside

Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-[(2R,3R,4S,5R,6R)-5-benzyloxy-2-benzyloxymethyl-4-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester