benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-2-(tert-butoxycarbonylamino)propanoate

Base Information

• Chemical Name: benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-2-(tert-butoxycarbonylamino)propanoate
• CAS No.: 78157-46-7
• Molecular Formula: C₂₉H₄₀N₂O₁₃
• Molecular Weight: 624.642
• Mol file: 78157-46-7.mol

Synonyms:benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-2-(tert-butoxycarbonylamino)propanoate

Chemical Property of benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-2-(tert-butoxycarbonylamino)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-2-(tert-butoxycarbonylamino)propanoate

There total 14 articles about benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-2-(tert-butoxycarbonylamino)propanoate 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: 85.0%

acetic anhydride (108-24-7) + (S)-2-tert-Butoxycarbonylamino-3-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-propionic acid benzyl ester → benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-2-(tert-butoxycarbonylamino)propanoate (78157-46-7)

Guidance literature:

With zinc; for 6h; Ambient temperature;

DOI:10.1039/a700210f

Reference yield: 27.0%

N-tert-butoxycarbonyl-L-serine benzyl ester (59524-02-6) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-2-(tert-butoxycarbonylamino)propanoate (78157-46-7)

Guidance literature:

With mercury(II) cyanide; In benzene; 1.) reflux; 2.) 18 h, reflux; 3.) 24 h, RT;

DOI:10.1016/S0008-6215(00)85248-9

Reference yield:

acetic anhydride (108-24-7) + N-tert-butoxycarbonyl-L-serine benzyl ester (59524-02-6) + O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate (136945-14-7) → benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-2-(tert-butoxycarbonylamino)propanoate (78157-46-7)

Guidance literature:

N-tert-butoxycarbonyl-L-serine benzyl ester; O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 1h;

acetic anhydride; With hydrogenchloride; zinc; In methanol; diethyl ether; at 20 ℃; for 6h;

upstream raw materials:

N-tert-butoxycarbonyl-L-serine benzyl ester

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

acetic anhydride

O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate