(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 benzyl ester

Base Information

• Chemical Name: (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 benzyl ester
• CAS No.: 196097-71-9
• Molecular Formula: C₄₁H₄₃Cl₃N₂O₁₄
• Molecular Weight: 894.156
• Mol file: 196097-71-9.mol

Synonyms:(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 benzyl ester

Chemical Property of (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 benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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 benzyl ester

There total 11 articles about (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 benzyl 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: 78.0%

N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester (73724-48-8) + ethyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside (144923-59-1) → (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 benzyl ester (196097-71-9)

Guidance literature:

With MS 4 Angstroem; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1021/ja971383c

Reference yield:

glucosamine (14257-69-3) → (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 benzyl ester (196097-71-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / 1 N NaOH

2: 90 percent / pyridine

3: 90 percent / HCl / acetone

4: 90 percent

5: 80 percent / BF₃*Et₂O

6: 40 percent / DMTST, molecular sieves

With pyridine; hydrogenchloride; sodium hydroxide; molecular sieve; boron trifluoride diethyl etherate; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In acetone;

DOI:10.1021/ja982312w

Reference yield:

Anisalglucosamin (51471-40-0) → (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 benzyl ester (196097-71-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / pyridine

2: 90 percent / HCl / acetone

3: 90 percent

4: 80 percent / BF₃*Et₂O

5: 40 percent / DMTST, molecular sieves

With pyridine; hydrogenchloride; molecular sieve; boron trifluoride diethyl etherate; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In acetone;

DOI:10.1021/ja982312w

upstream raw materials:

N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester

ethyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

glucosamine

Anisalglucosamin

Downstream raw materials:

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