N-(9H-fluoren-9-ylmethoxycarbonyl)-D-serine benzyl ester

Base Information

• Chemical Name: N-(9H-fluoren-9-ylmethoxycarbonyl)-D-serine benzyl ester
• CAS No.: 118358-66-0
• Molecular Formula: C₂₅H₂₃NO₅
• Molecular Weight: 417.461
• Mol file: 118358-66-0.mol

Synonyms:N-(9H-fluoren-9-ylmethoxycarbonyl)-D-serine benzyl ester

Chemical Property of N-(9H-fluoren-9-ylmethoxycarbonyl)-D-serine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(9H-fluoren-9-ylmethoxycarbonyl)-D-serine benzyl ester

There total 13 articles about N-(9H-fluoren-9-ylmethoxycarbonyl)-D-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: 96.0%

benzyl bromide (100-39-0) + N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester (118358-66-0,73724-46-6)

Guidance literature:

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine; With caesium carbonate; In tetrahydrofuran; water; at 20 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; for 3h;

DOI:10.1016/j.carres.2021.108495

Reference yield: 95.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-serine benzyl ester hydrochloride (60022-62-0,879278-55-4,151651-44-4) → N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester (118358-66-0,73724-46-6)

Guidance literature:

With N,N-diethyl-N-isopropylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo005712m

Reference yield: 87.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + L-serine benzyl ester hydrochloride (60022-62-0,879278-55-4,151651-44-4) → N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester (118358-66-0,73724-46-6)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; for 2h; Product distribution; other reactant;

DOI:10.1139/v82-146

upstream raw materials:

L-serine benzyl ester

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

L-serine benzyl ester hydrochloride

(fluorenylmethoxy)carbonyl chloride

Downstream raw materials:

benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate

C₅₁H₄₃NO₁₂

N-Fmoc-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-serine benzyl ester

N-9-fluorenylmethoxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-serine benzyl ester

Refernces

• 1、 Lapatsanis, Lucas,Milias, George,Froussios, Kleanthis,Kolovos, Miltiadis. "Synthesis of N-2,2,2-(Trichloroethoxycarbonyl)-L-amino Acids and N-(9-Fluorenylmethoxycarbonyl)-L-amino Acids Involving Succinimidoxy Anion as a Leaving Group in Amino Acid Protection". . p. 671 - 673. Retrieved 1983.
• 2、 -. "O-SUBSTITUTED SERINE DERIVATIVE PRODUCTION METHOD". . . Retrieved 2022/01/24.
• 3、 Batton, Chyree S.,Mukherjee, Jyoti P.,Roy, Joyeeta,Taylor, Carol M.,Wong, Douglas,Yadav, Saroj. "Progress toward the assembly of the bicyclic theonellamide skeleton". . . Retrieved 2020/04/01.