(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

Base Information

• Chemical Name: (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
• CAS No.: 174004-28-5
• Molecular Formula: C₃₉H₃₄Cl₃F₅N₂O₁₄
• Molecular Weight: 956.055
• Mol file: 174004-28-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 6 articles about (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 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%

Nα-(fluoren-9-ylmethoxycarbonyl)-L-serine pentafluorophenyl ester (86061-05-4) + Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-6-(trichloromethyl-carbamoyl)-tetrahydro-pyran-4-yl 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 (174004-28-5)

Guidance literature:

With 3 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane;

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

Reference yield: 85.0%

Nα-(fluoren-9-ylmethoxycarbonyl)-L-serine pentafluorophenyl ester (86061-05-4) + 3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide (67124-60-1) → (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)

Guidance literature:

With 3 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -40 ℃; for 2h;

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

Reference yield:

D-glucosamine hydrochloride (14131-63-6) → (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)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen carbonate / water

2: pyridine

3: hydrogen bromide; acetic acid

4: silver trifluoromethanesulfonate

With pyridine; hydrogen bromide; silver trifluoromethanesulfonate; hydrogen carbonate; acetic acid; In water;

upstream raw materials:

N^α-(fluoren-9-ylmethoxycarbonyl)-L-serine pentafluorophenyl ester

3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide

D-glucosamine hydrochloride

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose

Downstream raw materials:

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