5-[(1S)-1-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-methylpropyl]-3-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-oxadiazole

Base Information

• Chemical Name: 5-[(1S)-1-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-methylpropyl]-3-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-oxadiazole
• CAS No.: 915313-63-2
• Molecular Formula: C₅₅H₄₇N₃O₁₂
• Molecular Weight: 941.991
• Mol file: 915313-63-2.mol

Synonyms:

Chemical Property of 5-[(1S)-1-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-methylpropyl]-3-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-oxadiazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(1S)-1-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-methylpropyl]-3-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-oxadiazole

There total 4 articles about 5-[(1S)-1-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-methylpropyl]-3-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-oxadiazole 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: 51.0%

O-[(1S)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}valinoyl]-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)formamidoxime (915313-45-0) → 5-[(1S)-1-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-methylpropyl]-3-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-oxadiazole (915313-63-2)

Guidance literature:

In 1,4-dioxane; for 144h; Heating;

DOI:10.1002/ejoc.200600073

Reference yield:

C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)formamidoxime (915396-24-6) → 5-[(1S)-1-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-methylpropyl]-3-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-oxadiazole (915313-63-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / HOBt; EDCI / CH₂Cl₂; dimethylformamide / 8 h / 20 °C

2: 51 percent / dioxane / 144 h / Heating

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600073

Reference yield:

Fmoc-Val-OH (68858-20-8) → 5-[(1S)-1-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-methylpropyl]-3-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-oxadiazole (915313-63-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / HOBt; EDCI / CH₂Cl₂; dimethylformamide / 8 h / 20 °C

2: 51 percent / dioxane / 144 h / Heating

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600073

upstream raw materials:

O-[(1S)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}valinoyl]-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)formamidoxime

C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)formamidoxime

Fmoc-Val-OH

2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl cyanide