3-O-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester

Base Information

• Chemical Name: 3-O-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester
• CAS No.: 105678-34-0
• Molecular Formula: C₄₆H₅₄N₄O₁₅
• Molecular Weight: 902.953
• Mol file: 105678-34-0.mol

Synonyms:

Chemical Property of 3-O-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester

There total 11 articles about 3-O-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester 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: 26.0%

N-(Fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester (105678-38-4) + tetra-O-acetyl-β-D-xylopyranose (4049-33-6) → 3-O-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester (105678-34-0)

Guidance literature:

With calcium sulfate; mercury(II) cyanide; In benzene; for 2h; Heating;

DOI:10.1246/bcsj.54.621

Reference yield:

N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) → 3-O-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester (105678-34-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / Et₃N, EEDQ / CH₂Cl₂ / 1.) o deg C, 1 h, 2.) r.t., 20 h

2: HCOOH / Ambient temperature

3: 78 percent / EEDQ / CH₂Cl₂ / 1.) o deg C, 1 h, 2.) r.t., 20 h

4: HCOOH / Ambient temperature

5: EEDQ / CH₂Cl₂; dimethylformamide / 20 h / Ambient temperature

With formic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)90343-4

Reference yield:

N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester (118358-66-0,73724-46-6) → 3-O-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester (105678-34-0)

Guidance literature:

Multi-step reaction with 3 steps

1: AgClO₄, 4 Angstoem MS / toluene; CH₂Cl₂ / 18 h / Ambient temperature

2: Pd-Mohr, HCOOH / CH₂Cl₂ / 0.5 h / Ambient temperature

3: EEDQ / CH₂Cl₂; dimethylformamide / 20 h / Ambient temperature

With formic acid; 4 Angstoem MS; Pd-Mohr; silver perchlorate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0008-6215(00)90343-4

upstream raw materials:

[(2S,3S)-2-(2-Amino-acetylamino)-3-methyl-pentanoylamino]-acetic acid benzyl ester

Nα-(9-fluorenylmethoxycarbonyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-L-serine

N-(Fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester

tetra-O-acetyl-β-D-xylopyranose

Downstream raw materials:

3-O-(β-D-Xylopyranosyl)-L-seryl-glycyl-L-isoleucyl-glycin