N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-benzyl-β-D-xylopyranosyl)-L-serine benzyl ester

Base Information

• Chemical Name: N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-benzyl-β-D-xylopyranosyl)-L-serine benzyl ester
• CAS No.: 1415218-10-8
• Molecular Formula: C₅₁H₄₅NO₁₁
• Molecular Weight: 847.918
• Mol file: 1415218-10-8.mol

Synonyms:N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-benzyl-β-D-xylopyranosyl)-L-serine benzyl ester

Chemical Property of N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-benzyl-β-D-xylopyranosyl)-L-serine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-benzyl-β-D-xylopyranosyl)-L-serine benzyl ester

There total 10 articles about N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-benzyl-β-D-xylopyranosyl)-L-serine 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: 83.0%

p-tolyl 2,3-di-O-benzoyl-4-benzyl-1-thio-β-D-xylopyranose (1415218-05-1) + N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester (118358-66-0,73724-46-6) → N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-benzyl-β-D-xylopyranosyl)-L-serine benzyl ester (1415218-10-8)

Guidance literature:

p-tolyl 2,3-di-O-benzoyl-4-benzyl-1-thio-β-D-xylopyranose; With silver trifluoromethanesulfonate; In diethyl ether; dichloromethane; at -78 ℃; for 0.0833333h; Inert atmosphere; Molecular sieve;

With para-thiocresol; In diethyl ether; dichloromethane; at -78 ℃; for 0.0833333h; Inert atmosphere;

N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester; With 2,4,6-tri-tert-butylpyrimidine; In diethyl ether; dichloromethane; at -78 - 0 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.201205601

Reference yield:

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-benzyl-β-D-xylopyranosyl)-L-serine benzyl ester (1415218-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium hydrogencarbonate; tetra-(n-butyl)ammonium iodide / dimethyl sulfoxide / 8 h / 20 °C / Inert atmosphere

2.1: silver trifluoromethanesulfonate / dichloromethane; diethyl ether / 0.08 h / -78 °C / Inert atmosphere; Molecular sieve

2.2: 0.08 h / -78 °C / Inert atmosphere

2.3: 2 h / -78 - 0 °C / Inert atmosphere

With silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydrogencarbonate; In diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1002/anie.201205601

Reference yield:

benzyl bromide (100-39-0) → N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-benzyl-β-D-xylopyranosyl)-L-serine benzyl ester (1415218-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium hydrogencarbonate; tetra-(n-butyl)ammonium iodide / dimethyl sulfoxide / 8 h / 20 °C / Inert atmosphere

2.1: silver trifluoromethanesulfonate / dichloromethane; diethyl ether / 0.08 h / -78 °C / Inert atmosphere; Molecular sieve

2.2: 0.08 h / -78 °C / Inert atmosphere

2.3: 2 h / -78 - 0 °C / Inert atmosphere

With silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydrogencarbonate; In diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1002/anie.201205601

upstream raw materials:

benzoyl chloride

benzyl bromide

D-Xylose

p-methylphenyl 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranoside

Downstream raw materials:

N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-β-D-xylopyranosyl)-L-serine benzyl ester