N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-L-serine pentafluorophenyl ester

Base Information

• Chemical Name: N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-L-serine pentafluorophenyl ester
• CAS No.: 160410-57-1
• Molecular Formula: C38H35F5N2O13
• Molecular Weight: 822.694
• Mol file: 160410-57-1.mol

Synonyms:N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-L-serine pentafluorophenyl ester

Chemical Property of N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-L-serine pentafluorophenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-L-serine pentafluorophenyl ester

There total 18 articles about N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-L-serine pentafluorophenyl ester 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: 87.0%

pentafluorophenyl trifloroacetate (14533-84-7) + Nα-(9-flourenylmethoxycarbonyl)-3-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-Β-D-glucopyranosyl)-L-serine (160067-63-0) → O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-Nα-(fluoren-9-ylmethoxycarbonyl)-L-serine pentafluorophenyl ester (160410-57-1)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.8b02182

Reference yield: 80.0%

acetic anhydride (108-24-7) + Nα-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl)-L-serine pentafluorophenyl ester (162894-84-0) → O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-Nα-(fluoren-9-ylmethoxycarbonyl)-L-serine pentafluorophenyl ester (160410-57-1)

Guidance literature:

With acetic acid; zinc; In tetrahydrofuran; at 25 ℃; for 17h;

DOI:10.1021/ja953529i

Reference yield: 75.0%

acetic anhydride (108-24-7) + (S)-3-[(2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid pentafluorophenyl ester (174004-28-5) → O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-Nα-(fluoren-9-ylmethoxycarbonyl)-L-serine pentafluorophenyl ester (160410-57-1)

Guidance literature:

With zinc; In tetrahydrofuran; acetic acid; for 2h;

DOI:10.1016/0040-4039(95)01941-A

upstream raw materials:

acetic anhydride

N^α-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-L-serine pentafluorophenyl ester

(S)-3-[(2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid pentafluorophenyl ester

N^α-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl)-L-serine pentafluorophenyl ester

Refernces

• 1、 -. "Early detection of diabetes". . . Retrieved 2016/02/26.
• 2、 Jensen, Knud J.,Hansen, Paul R.,Venugopal,Barany, George. "Synthesis of 2-acetamido-2-deoxy-β-D-glucopyranose o-glycopeptides from N-dithiasuccinoyl-protected derivatives". . p. 3148 - 3155. Retrieved 2007/10/03.