N-(9-Fluorenylmethoxycarbonyl)-L-serine Phenacyl Ester

Base Information

• Chemical Name: N-(9-Fluorenylmethoxycarbonyl)-L-serine Phenacyl Ester
• CAS No.: 125760-26-1
• Molecular Formula: C26H23NO6
• Molecular Weight: 445.472
• DSSTox Substance ID: DTXSID10447048
• Nikkaji Number: J2.173.225G
• Wikidata: Q72478745
• Mol file: 125760-26-1.mol

Synonyms:125760-26-1;Fmoc-Ser-OPac;N-(9-Fluorenylmethoxycarbonyl)-L-serine Phenacyl Ester;phenacyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropanoate;L-Serine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 2-oxo-2-phenylethyl ester;2-oxo-2-phenylethyl (2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-hydroxypropanoate;DTXSID10447048;PYOVUIPZMRWLQC-QHCPKHFHSA-N;MFCD20264828;AKOS027446855;AS-73212;J-005283;N-(9-fluorenylmethyloxycarbonyl)-l-serine phenacylester;N-(9H-Fluorene-9-ylmethoxycarbonyl)-L-serine phenacyl ester;2-oxo-2-phenylethyl (((9H-fluoren-9-yl)methoxy)carbonyl)-L-serinate

Chemical Property of N-(9-Fluorenylmethoxycarbonyl)-L-serine Phenacyl Ester

Chemical Property:

• Vapor Pressure: 1.76E-20mmHg at 25°C
• Boiling Point: 698.5°C at 760 mmHg
• Flash Point: 376.2°C
• PSA: 105.42000
• Density: 1.304g/cm³
• LogP: 3.51650
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 445.15253745
• Heavy Atom Count: 33
• Complexity: 668

Purity/Quality:

98%min ^*data from raw suppliers

N-(9-Fluorenylmethoxycarbonyl)-L-serinePhenacylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)COC(=O)C(CO)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)COC(=O)[C@H](CO)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Uses: N-(9-Fluorenylmethoxycarbonyl)-L-serine Phenacyl Ester is used in preparation of protected Serine.Also, used in preparation of Glycoside Glycosylceramide analogs as immunomodulators and antitumor agents.

Technology Process of N-(9-Fluorenylmethoxycarbonyl)-L-serine Phenacyl Ester

There total 1 articles about N-(9-Fluorenylmethoxycarbonyl)-L-serine Phenacyl 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: 68.0%

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) + α-bromoacetophenone (70-11-1) → N-Fmoc serine phenacyl ester (125760-26-1)

Guidance literature:

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine; With N-cyclohexyl-cyclohexanamine; In ethyl acetate; at 20 ℃; for 2h;

α-bromoacetophenone; With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 3.5h;

DOI:10.1021/acschembio.5b00972

Reference yield: 80.0%

2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-D-mannopyranosyl fluoride + N-Fmoc serine phenacyl ester (125760-26-1) → N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-mannopyranosyl]-L-serine phenacyl ester (1192143-24-0) + N-(9-fluorenylmethoxycarbonyl)-O-[2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-L-serine phenacyl ester (1192142-94-1)

Guidance literature:

With zirconocene dichloride; silver perchlorate; In dichloromethane; at -40 - 0 ℃; for 3h; stereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tet.2009.07.080

Reference yield: 80.0%

N-Fmoc serine phenacyl ester (125760-26-1) + 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl 2,2,2-trichloroacetimidate (618115-57-4) → Nα-fluoren-9-ylmethoxycarbonyl-3-O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine phenacyl ester (848701-29-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tetasy.2004.12.003

upstream raw materials:

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine

α-bromoacetophenone

Downstream raw materials:

(S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester

Fmoc-Ser(bu^t)-O-Pha

(S)-3-[(2S,4aR,6S,7R,8R,8aR)-7-Acetylamino-2-phenyl-8-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester

N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine phenacyl ester

Refernces

• 1、 Wakamiya, Tateaki,Nishida, Takatoshi,Togashi, Ryusaku,Saruta, Kunio,Yasuoka, Jun-Ichi,Kusumoto, Shoichi. "Preparations of Nα-Fmoc-O-[(benzyloxy)hydroxyphosphinyl] β-hydroxy α-amino acid derivatives". . p. 465 - 468. Retrieved 2007/10/03.
• 2、 Fischer, Peter M.. "Application of t-Butyldimethylsilyl Ethers of Serine, Threonine and Tyrosine in Peptide Synthesis". . p. 7605 - 7608. Retrieved 2007/10/02.