2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

Base Information

Chemical Name:2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol
CAS No.:1354914-13-8
Molecular Formula:C₅₃H₅₇NO₁₀
Molecular Weight:868.036
Hs Code.:

Synonyms:2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

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Chemical Property of 2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

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Technology Process of 2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

There total 7 articles about 2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol 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: 94.0%

: 1354914-09-2
1-O-tert-butyldiphenylsilyl-2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

: 1354914-13-8
2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 16h; Inert atmosphere;
DOI:10.1021/ol2033652

Reference yield:

: 100-39-0
benzyl bromide

: 1354914-13-8
2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 30 h / 20 °C / Inert atmosphere

2.1: trimethylphosphane / 1,4-dioxane; water; toluene / 4 h / 20 °C / Inert atmosphere

3.1: pyridine / 16 h / 20 °C / Inert atmosphere

4.1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere

4.2: 0.5 h / 20 °C / Inert atmosphere

5.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

With pyridine; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; triethylamine; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1021/ol2033652

Reference yield:

: 544686-89-7
3-O-allyl-2-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

: 1354914-13-8
2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

Guidance literature:: Multi-step reaction with 5 steps

1.1: trimethylphosphane / 1,4-dioxane; water; toluene / 4 h / 20 °C / Inert atmosphere

2.1: pyridine / 16 h / 20 °C / Inert atmosphere

3.1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere

3.2: 0.5 h / 20 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

With pyridine; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; tetrabutyl ammonium fluoride; hydrogen; triethylamine; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene;
DOI:10.1021/ol2033652