1-([N,N,-diisopropylamino]-2-cyanoethylphosphite)-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:1-([N,N,-diisopropylamino]-2-cyanoethylphosphite)-2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol
CAS No.:1354914-10-5
Molecular Formula:C₆₂H₇₄N₃O₁₁P
Molecular Weight:1068.26
Hs Code.:

1-([N,N,-diisopropylamino]-2-cyanoethylphosphite)-2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

Synonyms:1-([N,N,-diisopropylamino]-2-cyanoethylphosphite)-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 1-([N,N,-diisopropylamino]-2-cyanoethylphosphite)-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 1-([N,N,-diisopropylamino]-2-cyanoethylphosphite)-2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

There total 8 articles about 1-([N,N,-diisopropylamino]-2-cyanoethylphosphite)-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: 75.0%

: 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

: 124482-92-4,89992-70-1
2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

: 1354914-10-5
1-([N,N,-diisopropylamino]-2-cyanoethylphosphite)-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 triethylamine; In dichloromethane; at 0 ℃; Inert atmosphere;
DOI:10.1021/ol2033652

Reference yield:

: 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

: 1354914-10-5
1-([N,N,-diisopropylamino]-2-cyanoethylphosphite)-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 2 steps

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

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

With tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol2033652

Reference yield:

: 100-39-0
benzyl bromide

: 1354914-10-5
1-([N,N,-diisopropylamino]-2-cyanoethylphosphite)-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 7 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

7.1: triethylamine / dichloromethane / 0 °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