N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-L-serine pentafluorophenyl ester

Base Information

• Chemical Name: N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-L-serine pentafluorophenyl ester
• CAS No.: 291311-49-4
• Molecular Formula: C₂₅H₁₈F₅NO₅
• Molecular Weight: 507.414
• Mol file: 291311-49-4.mol

Synonyms:N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-L-serine pentafluorophenyl ester

Chemical Property of N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-L-serine pentafluorophenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-L-serine pentafluorophenyl ester

There total 2 articles about N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-L-serine pentafluorophenyl 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: 89.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + Fmoc-N-methyl-L-serine (291311-48-3) → Nα-(fluoren-9-ylmethoxycarbonyl)-Nα-methyl-L-serine pentafluorophenyl ester (291311-49-4)

Guidance literature:

With dacarbazine; In ethyl acetate; at 0 - 20 ℃;

DOI:10.1016/S0040-4039(00)00611-0

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Nα-(fluoren-9-ylmethoxycarbonyl)-Nα-methyl-L-serine pentafluorophenyl ester (291311-49-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / Et₃N / acetonitrile; H₂O / 20 °C

2: 89 percent / DIC / ethyl acetate / 0 - 20 °C

With dacarbazine; triethylamine; In water; ethyl acetate; acetonitrile; 1: Acylation / 2: Esterification;

DOI:10.1016/S0040-4039(00)00611-0

Reference yield: 91.0%

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) + Nα-(fluoren-9-ylmethoxycarbonyl)-Nα-methyl-L-serine pentafluorophenyl ester (291311-49-4) → Nα-(fluoren-9-ylmethoxycarbonyl)-Nα-methyl-3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester (343309-00-2)

Guidance literature:

With 3 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -30 ℃; for 3h;

DOI:10.1021/jo001584q

upstream raw materials:

2,3,4,5,6-pentafluorophenol

Fmoc-N-methyl-L-serine

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

Downstream raw materials:

(S)-2-[(9H-Fluoren-9-ylmethoxycarbonyl)-methyl-amino]-3-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid pentafluorophenyl ester

N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester

N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-(4-fluorobenzoyl)-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester

N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-(3-fluorobenzoyl)-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester