2-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}amino)-3-hydroxypropanoate

Base Information

• Chemical Name: 2-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}amino)-3-hydroxypropanoate
• CAS No.: 73724-45-5
• Molecular Formula: C18H17NO5
• Molecular Weight: 327.337
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID60994597
• Wikidata: Q72478889
• Mol file: 73724-45-5.mol

Synonyms:DTXSID60994597;2-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}amino)-3-hydroxypropanoate

Chemical Property of 2-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}amino)-3-hydroxypropanoate

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 3.27E-15mmHg at 25°C
• Melting Point: 104-106 °C
• Refractive Index: -12.5 ° (C=1, DMF)
• Boiling Point: 599.3 °C at 760 mmHg
• PKA: 3.51±0.10(Predicted)
• Flash Point: 316.2 °C
• PSA: 95.86000
• Density: 1.362 g/cm³
• LogP: 2.36150
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 326.10284761
• Heavy Atom Count: 24
• Complexity: 441

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-Ser ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CO)C(=O)[O-]
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CO)C(=O)[O-]
• Uses: N-Fmoc-L-serine is an N-Fmoc-protected form of L-Serine (S270975). L-Serine is a nonessential amino acid that is required for the synthesis of sphingolipids and phosphatidylserine, compounds that are important for central nervous system neuronal survival. L-Serine is also important in intermediary metabolism in eukaryotic cells.

Technology Process of 2-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}amino)-3-hydroxypropanoate

There total 35 articles about 2-({[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}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: 100.0%

L-serin (56-45-1,83245-15-2) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5)

Guidance literature:

With sodium hydrogencarbonate;

DOI:10.1002/ejoc.201100304

Reference yield: 99.0%

Fmoc-Ser(tBu)-OH (71989-33-8) → N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; for 0.25h; Ambient temperature;

DOI:10.1016/S0040-4039(00)79116-7

Reference yield: 95.0%

N-9-fluorenylmethoxycarbonyl-O-trityl-L-serine methyl ester (171820-89-6) → N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5)

Guidance literature:

With sodium thiosulfate; magnesium iodide; In 2-methyltetrahydrofuran; at 120 ℃; for 2h; chemoselective reaction; Microwave irradiation; Inert atmosphere;

DOI:10.1002/bip.22908

upstream raw materials:

D-Serine

(fluorenylmethoxy)carbonyl chloride

N-(9-fluorenylmethoxycarbonyl)-DL-serine

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

Downstream raw materials:

O-(Acetoacetyl)-N-(9-fluorenylmethoxycarbonyl)-L-serin

N^α-(9-flourenylmethoxycarbonyl)-3-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-Β-D-glucopyranosyl)-L-serine

(S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionylamino]-hex-5-enoic acid benzyl ester

Refernces

• 1、 -. "O-SUBSTITUTED SERINE DERIVATIVE PRODUCTION METHOD". . . Retrieved 2022/01/24.
• 2、 Senko, Dmitry A.,Timofeev, Nikita D.,Kasheverov, Igor E.,Ivanov, Igor A.. "Scope and limitations of pseudoprolines as individual amino acids in peptide synthesis". . p. 665 - 671. Retrieved 2021/04/09.