(2S)-2-O-(2,3,4,6-tetra-O-benzyl-a-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-1-glyceryl succinate

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Chemical Name:(2S)-2-O-(2,3,4,6-tetra-O-benzyl-a-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-1-glyceryl succinate
CAS No.:1384160-49-9
Molecular Formula:C₆₂H₆₄O₁₃
Molecular Weight:1017.18
Hs Code.:

Synonyms:(2S)-2-O-(2,3,4,6-tetra-O-benzyl-a-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-1-glyceryl succinate

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Chemical Property of (2S)-2-O-(2,3,4,6-tetra-O-benzyl-a-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-1-glyceryl succinate

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Technology Process of (2S)-2-O-(2,3,4,6-tetra-O-benzyl-a-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-1-glyceryl succinate

There total 5 articles about (2S)-2-O-(2,3,4,6-tetra-O-benzyl-a-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-1-glyceryl succinate 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: 96.0%

: 108-30-5
succinic acid anhydride

: 1384160-47-7
2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

: 1384160-49-9
(2S)-2-O-(2,3,4,6-tetra-O-benzyl-a-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-1-glyceryl succinate

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.carres.2012.02.023

Reference yield:

: 1384160-41-1
C₅₀H₄₄F₃NO₈

: 1384160-49-9
(2S)-2-O-(2,3,4,6-tetra-O-benzyl-a-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-1-glyceryl succinate

Guidance literature:: Multi-step reaction with 7 steps

1.1: trifluorormethanesulfonic acid / diethyl ether / 0.42 h / 0 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere

4.1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

4.2: 1.5 h / 20 °C / Inert atmosphere

5.1: triethylamine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 2.5 h / 0 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

7.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

With (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.carres.2012.02.023

Reference yield:

: 1384160-46-6
2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-O-(tert-butyldiphenylsilyl)-sn-glycerol

: 1384160-49-9
(2S)-2-O-(2,3,4,6-tetra-O-benzyl-a-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-1-glyceryl succinate

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 2.5 h / 0 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

3: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran;
DOI:10.1016/j.carres.2012.02.023