methyl 2α-O-(N-fluorenonemethyoxycarbonyl)-phenyglycylurs-3β,23-isopropylidenedioxyurs-12-ene-28-oate

Base Information

• Chemical Name: methyl 2α-O-(N-fluorenonemethyoxycarbonyl)-phenyglycylurs-3β,23-isopropylidenedioxyurs-12-ene-28-oate
• CAS No.: 1575689-22-3
• Molecular Formula: C₅₇H₇₁NO₈
• Molecular Weight: 898.193
• Mol file: 1575689-22-3.mol

Synonyms:methyl 2α-O-(N-fluorenonemethyoxycarbonyl)-phenyglycylurs-3β,23-isopropylidenedioxyurs-12-ene-28-oate

Chemical Property of methyl 2α-O-(N-fluorenonemethyoxycarbonyl)-phenyglycylurs-3β,23-isopropylidenedioxyurs-12-ene-28-oate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2α-O-(N-fluorenonemethyoxycarbonyl)-phenyglycylurs-3β,23-isopropylidenedioxyurs-12-ene-28-oate

There total 4 articles about methyl 2α-O-(N-fluorenonemethyoxycarbonyl)-phenyglycylurs-3β,23-isopropylidenedioxyurs-12-ene-28-oate 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: 54.03%

methyl 2α-hydroxy-3β,23-isopropylidenedioxyurs-12-ene-28-oate (19533-98-3) + N-Fmoc-D-phenylglycine (111524-95-9,163883-97-4) → methyl 2α-O-(N-fluorenonemethyoxycarbonyl)-phenyglycylurs-3β,23-isopropylidenedioxyurs-12-ene-28-oate (1575689-22-3)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1248/cpb.c13-00328

Reference yield:

asiatic acid (464-92-6,89786-83-4,103974-74-9,106327-64-4,114580-55-1,116348-15-3,143839-02-5) → methyl 2α-O-(N-fluorenonemethyoxycarbonyl)-phenyglycylurs-3β,23-isopropylidenedioxyurs-12-ene-28-oate (1575689-22-3)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 5 h / 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 6 h / 20 °C

3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 0 - 20 °C

With dmap; potassium carbonate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.c13-00328

Reference yield:

2α-hydroxy-3β,23-isopropylidenedioxy-urs-12-ene-28-oic acid (139610-49-4) → methyl 2α-O-(N-fluorenonemethyoxycarbonyl)-phenyglycylurs-3β,23-isopropylidenedioxyurs-12-ene-28-oate (1575689-22-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 20 °C

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 0 - 20 °C

With dmap; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.c13-00328

upstream raw materials:

methyl 2α-hydroxy-3β,23-isopropylidenedioxyurs-12-ene-28-oate

N-Fmoc-D-phenylglycine

asiatic acid

2α-hydroxy-3β,23-isopropylidenedioxy-urs-12-ene-28-oic acid

Downstream raw materials:

methyl 2-O-phenyglycylurs-3,23-isopropylidenedioxyurs-12-ene-28-oate