benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside

Base Information

Chemical Name:benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside
CAS No.:81086-81-9
Molecular Formula:C₄₀H₅₀N₄O₁₂
Molecular Weight:778.857
Hs Code.:

Synonyms:benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside

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Chemical Property of benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside

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Technology Process of benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside

There total 5 articles about benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside 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%

: 81100-12-1
benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside

: 81086-81-9
benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside

Guidance literature:: With acetic acid; at 40 - 45 ℃;
DOI:10.1016/S0008-6215(00)80680-1

Reference yield:

: 58886-40-1
benzyl 2-(benzyloxycarbonyl)amino-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside

: 81086-81-9
benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 77 percent / lithium aluminium hydride / tetrahydrofuran / 19 h / Heating

2: 88 percent / 0.5 M sodium carbonate / dioxane / 1.5 h / 0 °C

3: 60 percent / sodium hydride / dioxane / 2.5 h / 60 °C

4: 1.) dicyclohexylcarbodiimide, N-hydroxysuccinimide; 2.) triethylamine / 1.) 1,4-dioxane; 2.) 1,4-dioxane

5: 94 percent / 60 percent aq. acetic acid / 40 - 45 °C

With 1-hydroxy-pyrrolidine-2,5-dione; lithium aluminium tetrahydride; sodium hydride; sodium carbonate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane;
DOI:10.1016/S0008-6215(00)80680-1

Reference yield:

: 81086-76-2
benzyl 2-deoxy-5,6-O-isopropylidene-2-methylamino-β-D-glucofuranoside

: 81086-81-9
benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / 0.5 M sodium carbonate / dioxane / 1.5 h / 0 °C

2: 60 percent / sodium hydride / dioxane / 2.5 h / 60 °C

3: 1.) dicyclohexylcarbodiimide, N-hydroxysuccinimide; 2.) triethylamine / 1.) 1,4-dioxane; 2.) 1,4-dioxane

4: 94 percent / 60 percent aq. acetic acid / 40 - 45 °C

With 1-hydroxy-pyrrolidine-2,5-dione; sodium hydride; sodium carbonate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; In 1,4-dioxane;
DOI:10.1016/S0008-6215(00)80680-1