benzyl 2-acetamido-4-O-(6-acetamido-6-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside

Base Information

Chemical Name:benzyl 2-acetamido-4-O-(6-acetamido-6-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside
CAS No.:83116-29-4
Molecular Formula:C₄₁H₅₇N₅O₁₆
Molecular Weight:875.927
Hs Code.:

benzyl 2-acetamido-4-O-(6-acetamido-6-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside

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Chemical Property of benzyl 2-acetamido-4-O-(6-acetamido-6-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside

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Technology Process of benzyl 2-acetamido-4-O-(6-acetamido-6-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside

There total 10 articles about benzyl 2-acetamido-4-O-(6-acetamido-6-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-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:

: 66530-19-6
(R)-2-[(2S,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-6-hydroxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionic acid methyl ester

: 83116-29-4
benzyl 2-acetamido-4-O-(6-acetamido-6-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: p-TsOH*H₂O / dimethylformamide / 2 h / 50 °C

2: pyridine

3: 60percent acetic acid / H₂O / 1 h / 50 °C

4: 310 mg / pyridine / 5 h / -25 °C

5: pyridine

6: 208 mg / sodium azide / dimethylformamide / 6 h / 60 °C

7: 1.) H₂ / 1.) 10percent Pd-C / 1.) methanol, room temperature, 2 h; 2.) methanol, 2 h

8: 99 mg / sodium methoxide / methanol / 0.05 h / Ambient temperature

9: 0.1 M aq. potassium hydroxide / dioxane; H₂O / 0.17 h / Ambient temperature

10: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide; 2.) triethylamine / 1.) N,N-dimethylformamide, room temperature, 1 h; 2.) N,N-dimethylformamide, room temperature, overnight

With pyridine; potassium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; sodium azide; hydrogen; sodium methylate; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)82587-2

Reference yield:

: (R)-2-[(2S,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-5-((4aR,6S,7R,8R,8aS)-7,8-dihydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-propionic acid methyl ester

: 83116-29-4
benzyl 2-acetamido-4-O-(6-acetamido-6-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine

2: 60percent acetic acid / H₂O / 1 h / 50 °C

3: 310 mg / pyridine / 5 h / -25 °C

4: pyridine

5: 208 mg / sodium azide / dimethylformamide / 6 h / 60 °C

6: 1.) H₂ / 1.) 10percent Pd-C / 1.) methanol, room temperature, 2 h; 2.) methanol, 2 h

7: 99 mg / sodium methoxide / methanol / 0.05 h / Ambient temperature

8: 0.1 M aq. potassium hydroxide / dioxane; H₂O / 0.17 h / Ambient temperature

9: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide; 2.) triethylamine / 1.) N,N-dimethylformamide, room temperature, 1 h; 2.) N,N-dimethylformamide, room temperature, overnight

With pyridine; potassium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; sodium azide; hydrogen; sodium methylate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)82587-2

Reference yield:

: 83100-77-0
benzyl 2-acetamido-6-O-benzoyl-4-O-(2,3-di-O-benzoyl-β-D-glucopyranosyl)-2-deoxy-3-O--α-D-glucopyranoside

: 83116-29-4
benzyl 2-acetamido-4-O-(6-acetamido-6-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 310 mg / pyridine / 5 h / -25 °C

2: pyridine

3: 208 mg / sodium azide / dimethylformamide / 6 h / 60 °C

4: 1.) H₂ / 1.) 10percent Pd-C / 1.) methanol, room temperature, 2 h; 2.) methanol, 2 h

5: 99 mg / sodium methoxide / methanol / 0.05 h / Ambient temperature

6: 0.1 M aq. potassium hydroxide / dioxane; H₂O / 0.17 h / Ambient temperature

7: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide; 2.) triethylamine / 1.) N,N-dimethylformamide, room temperature, 1 h; 2.) N,N-dimethylformamide, room temperature, overnight

With pyridine; potassium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; sodium azide; hydrogen; sodium methylate; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)82587-2