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
Hs Code.:

Synonyms:

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

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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%

: 105678-38-4
N-(Fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester

: 4049-33-6
tetra-O-acetyl-β-D-xylopyranose

: 105678-34-0
3-O-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester

Guidance literature:: With calcium sulfate; mercury(II) cyanide; In benzene; for 2h; Heating;
DOI:10.1246/bcsj.54.621

Reference yield:

: 13139-16-7
N-(tert-butyloxycarbonyl)-L-isoleucine

: 105678-34-0
3-O-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester

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:

: 118358-66-0,73724-46-6
N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester

: 105678-34-0
3-O-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester

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