2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-6-deoxy-2,3-di-O-(p-methoxybenzyl)-6-methylseleno-β-D-glucopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-6-deoxy-2,3-di-O-(p-methoxybenzyl)-6-methylseleno-β-D-glucopyranoside
CAS No.:1595121-65-5
Molecular Formula:C₆₂H₆₈O₁₆SeSi
Molecular Weight:1176.26
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-6-deoxy-2,3-di-O-(p-methoxybenzyl)-6-methylseleno-β-D-glucopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-6-deoxy-2,3-di-O-(p-methoxybenzyl)-6-methylseleno-β-D-glucopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-6-deoxy-2,3-di-O-(p-methoxybenzyl)-6-methylseleno-β-D-glucopyranoside

There total 9 articles about 2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-6-deoxy-2,3-di-O-(p-methoxybenzyl)-6-methylseleno-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%

: 1595121-62-2
2-(trimethylsilyl)ethyl 6-deoxy-2,3-di-O-(pmethoxybenzyl)-6-methylseleno-β-D-glucopyranoside

: 203435-09-0
2,3,4,6-tetra-O-benzoyl-α,b-D-galactopyranosyl trichloroacetimidate

: 1595121-65-5
2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-6-deoxy-2,3-di-O-(p-methoxybenzyl)-6-methylseleno-β-D-glucopyranoside

Guidance literature:: 2-(trimethylsilyl)ethyl 6-deoxy-2,3-di-O-(pmethoxybenzyl)-6-methylseleno-β-D-glucopyranoside; 2,3,4,6-tetra-O-benzoyl-α,b-D-galactopyranosyl trichloroacetimidate; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 14h; Inert atmosphere; Molecular sieve;
DOI:10.1016/j.bmc.2014.02.023

Reference yield:

: 1595121-53-1
2-(trimethylsilyl)ethyl 2,3-di-O-(p-methoxybenzyl)-β-D-glucopyranoside

: 1595121-65-5
2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-6-deoxy-2,3-di-O-(p-methoxybenzyl)-6-methylseleno-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: carbon tetrabromide; triphenylphosphine / pyridine / 1.17 h / 65 °C / Inert atmosphere; Cooling with ice

2.1: N-ethyl-N,N-diisopropylamine; piperidine / N,N-dimethyl-formamide / 0.75 h / 60 °C / Inert atmosphere

3.1: pyridine / 17 h / 20 °C / Inert atmosphere; Cooling with ice

4.1: methylhydrazine; caesium carbonate / N,N-dimethyl-formamide / 0.42 h / 20 °C / Inert atmosphere

5.1: sodium methylate; methanol / 44 h / 20 °C / Inert atmosphere

6.1: dichloromethane / 2 h / 20 °C / Inert atmosphere; Molecular sieve

6.2: 14 h / 0 °C / Inert atmosphere; Molecular sieve

With piperidine; methanol; carbon tetrabromide; sodium methylate; caesium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; methylhydrazine; In pyridine; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2014.02.023

Reference yield:

: 1595121-54-2
2-(trimethylsilyl)ethyl 6-bromo-6-deoxy-2,3-di-O-(pmethoxybenzyl)-β-D-glucopyranoside

: 1595121-65-5
2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-6-deoxy-2,3-di-O-(p-methoxybenzyl)-6-methylseleno-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-ethyl-N,N-diisopropylamine; piperidine / N,N-dimethyl-formamide / 0.75 h / 60 °C / Inert atmosphere

2.1: pyridine / 17 h / 20 °C / Inert atmosphere; Cooling with ice

3.1: methylhydrazine; caesium carbonate / N,N-dimethyl-formamide / 0.42 h / 20 °C / Inert atmosphere

4.1: sodium methylate; methanol / 44 h / 20 °C / Inert atmosphere

5.1: dichloromethane / 2 h / 20 °C / Inert atmosphere; Molecular sieve

5.2: 14 h / 0 °C / Inert atmosphere; Molecular sieve

With piperidine; methanol; sodium methylate; caesium carbonate; N-ethyl-N,N-diisopropylamine; methylhydrazine; In pyridine; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2014.02.023