(S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxypropanoate

Base Information

• Chemical Name: (S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxypropanoate
• CAS No.: 82911-78-2
• Molecular Formula: C19H19 N O5
• Molecular Weight: 341.364
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID30427286
• Nikkaji Number: J975.246C
• Wikidata: Q72478892
• Mol file: 82911-78-2.mol

Synonyms:82911-78-2;Fmoc-Ser-OMe;(S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxypropanoate;Fmoc-L-serine methyl ester;methyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropanoate;Serine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, methyl ester;MFCD00672334;N-Fmoc-L-Serine methyl ester;SCHEMBL1486273;DTXSID30427286;(S)-Methyl2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxypropanoate;AKOS016008217;HY-W072147;AS-19668;CS-0103666;C78493;EN300-5171403;A864325;Methyl (((9H-fluoren-9-yl)methoxy)carbonyl)-L-serinate;N-alpha-(9-Fluorenylmethoxycarbonyl)-L-serine methyl ester;Nalpha -(9-fluorenylmethoxycarbonyl)-L-serine methyl ester;methyl (2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-hydroxypropanoate

Chemical Property of (S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxypropanoate

Chemical Property:

• Boiling Point: 579.4±45.0 °C(Predicted)
• PKA: 10.07±0.46(Predicted)
• PSA: 88.35000
• Density: 1.285±0.06 g/cm3(Predicted)
• LogP: 2.26340
• Storage Temp.: -15°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 341.12632271
• Heavy Atom Count: 25
• Complexity: 460

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fmoc-Ser-OMe ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CO)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: COC(=O)[C@H](CO)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Technology Process of (S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxypropanoate

There total 9 articles about (S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxypropanoate 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: 98.0%

methanol (67-56-1) + N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester (82911-78-2)

Guidance literature:

With thionyl chloride; at 0 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acs.orglett.9b00626

Reference yield: 94.7%

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) + methyl iodide (74-88-4) → N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester (82911-78-2)

Guidance literature:

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

methyl iodide; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/jo9000993

Reference yield: 92.0%

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester (82911-78-2)

Guidance literature:

With Dowex; In methanol; Inert atmosphere; Reflux;

DOI:10.1016/j.jcat.2018.02.027

upstream raw materials:

methanol

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

methyl iodide

trifluoroacetic acid

Downstream raw materials:

Nα-(9-fluorenylmethoxycarbonyl)-O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester

(2S)-2-(fluorenylmethoxycarbonylamino)-3-(5'-bromo-2'-pyridyl)propionic acid

(2S)-(N-fluorenylmethoxycarbonylamino)-3-(pyrid-2'-yl)propionic acid

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-iodo-propionic acid methyl ester

Refernces

• 1、 Cheng, Xionglve,Jiang, Gangzhong,Li, Xingxing,Tao, Suyan,Wan, Xiaobing,Zhao, Yanwei,Zheng, Yonggao. "Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite". supporting information. p. 2713 - 2718. Retrieved 2021/06/25.
• 2、 Ghosh, Titli,Mukherji, Ananya,Kancharla, Pavan K.. "Sterically Hindered 2,4,6-Tri- tert-butylpyridinium Salts as Single Hydrogen Bond Donors for Highly Stereoselective Glycosylation Reactions of Glycals". supporting information. p. 3490 - 3495. Retrieved 2019/05/24.