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

Base Information

• Chemical Name: O-[(1S)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}valinoyl]-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)formamidoxime
• CAS No.: 915313-45-0
• Molecular Formula: C₅₅H₄₉N₃O₁₃
• Molecular Weight: 960.006

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

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

Chemical Property:

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

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

C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)formamidoxime (915396-24-6) + Fmoc-Val-OH (68858-20-8) → 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)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 8h;

DOI:10.1002/ejoc.200600073

Reference yield:

2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl cyanide (286369-05-9) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / hydroxylamine hydrochloride; pyridine / 8 h / 50 °C

2: 75 percent / HOBt; EDCI / CH₂Cl₂; dimethylformamide / 8 h / 20 °C

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

DOI:10.1002/ejoc.200600073

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

upstream raw materials:

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

Downstream raw materials:

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

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