benzyl N-trichloroethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-N-trichloroethoxycarbonyl-β-D-glucopyranosyl]-L-serinate

Base Information

• Chemical Name: benzyl N-trichloroethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-N-trichloroethoxycarbonyl-β-D-glucopyranosyl]-L-serinate
• CAS No.: 640291-21-0
• Molecular Formula: C₂₈H₃₂Cl₆N₂O₁₄
• Molecular Weight: 833.285
• Mol file: 640291-21-0.mol

Synonyms:benzyl N-trichloroethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-N-trichloroethoxycarbonyl-β-D-glucopyranosyl]-L-serinate

Chemical Property of benzyl N-trichloroethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-N-trichloroethoxycarbonyl-β-D-glucopyranosyl]-L-serinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl N-trichloroethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-N-trichloroethoxycarbonyl-β-D-glucopyranosyl]-L-serinate

There total 6 articles about benzyl N-trichloroethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-N-trichloroethoxycarbonyl-β-D-glucopyranosyl]-L-serinate 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%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose (122210-05-3) + benzyl N-(2,2,2-trichloroethoxycarbonyl)-L-serine (82911-81-7) → benzyl N-trichloroethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-N-trichloroethoxycarbonyl-β-D-glucopyranosyl]-L-serinate (640291-21-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; stereoselective reaction;

DOI:10.1016/j.bmcl.2008.09.060

Reference yield:

benzyl N-(2,2,2-trichloroethoxycarbonyl)-L-serine (82911-81-7) + 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose (122210-01-9,122210-05-3,145416-95-1,146864-65-5,114360-77-9) → benzyl N-trichloroethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-N-trichloroethoxycarbonyl-β-D-glucopyranosyl]-L-serinate (640291-21-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 48h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.0c00851

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → benzyl N-trichloroethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-N-trichloroethoxycarbonyl-β-D-glucopyranosyl]-L-serinate (640291-21-0)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / tetrachloromethane / 100 °C / Dean-Stark

2: triethylamine / dichloromethane / 1 h / Inert atmosphere

3: boron trifluoride diethyl etherate / dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere

With boron trifluoride diethyl etherate; toluene-4-sulfonic acid; triethylamine; In tetrachloromethane; dichloromethane;

DOI:10.1021/acs.jmedchem.0c00851

upstream raw materials:

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

benzyl N-(2,2,2-trichloroethoxycarbonyl)-L-serine

(+)-D-glucosamine hydrochloride

benzyl alcohol