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

Base Information

• Chemical Name: O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)-L-threonine pentafluorophenyl ester
• CAS No.: 160496-84-4
• Molecular Formula: C₃₉H₃₇F₅N₂O₁₃
• Molecular Weight: 836.72

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

Chemical Property of O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)-L-threonine pentafluorophenyl ester

Chemical Property:

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Technology Process of O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)-L-threonine pentafluorophenyl ester

There total 16 articles about O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)-L-threonine 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%

acetic anhydride (108-24-7) + Nα-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl)-L-threonine pentafluorophenyl ester (162894-85-1) → O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-Nα-(fluoren-9-ylmethoxycarbonyl)-L-threonine pentafluorophenyl ester (160496-84-4)

Guidance literature:

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

DOI:10.1021/ja953529i

Reference yield: 78.0%

acetic anhydride (108-24-7) + (2S,3R)-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)-butyric acid pentafluorophenyl ester (174004-29-6) → O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-Nα-(fluoren-9-ylmethoxycarbonyl)-L-threonine pentafluorophenyl ester (160496-84-4) + Acetic acid (2R,3S,4R,4aR,7S,8S,9aR)-3-acetoxy-2-acetoxymethyl-7-(9H-fluoren-9-ylmethoxycarbonylamino)-8-methyl-6-oxo-octahydro-1,9-dioxa-5-aza-benzocyclohepten-4-yl ester

Guidance literature:

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

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

Reference yield: 74.0%

pentafluorophenyl trifloroacetate (14533-84-7) + Nα-fluoren-9-ylmethoxycarbonyl-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-threonine (160168-40-1) → O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-Nα-(fluoren-9-ylmethoxycarbonyl)-L-threonine pentafluorophenyl ester (160496-84-4)

Guidance literature:

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

DOI:10.1021/acs.orglett.8b02182

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-threonine pentafluorophenyl ester

(2S,3R)-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)-butyric acid pentafluorophenyl ester

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

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