N-Fmoc-O-tert-butyl-DL-serine

Base Information

• Chemical Name: N-Fmoc-O-tert-butyl-DL-serine
• CAS No.: 71989-33-8
• Molecular Formula: C22H25NO5
• Molecular Weight: 383.444
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID40868060
• Mol file: 71989-33-8.mol

Synonyms:N-Fmoc-O-tert-butyl-DL-serine;205812-07-3;3-(tert-butoxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid;EINECS 276-260-6;Fmoc-O-(tert-butyl)-L-serine;MFCD00077071;O-(tert-Butyl)-N-((9H-fluoren-9-ylmethoxy)carbonyl)-L-serine;SCHEMBL598209;N-Fmoc-O-tert-butyl-D-Serine;DTXSID40868060;AKOS032947705;SY021360;SY029768;FT-0601883;FT-0601939;C78033;EN300-297237;O-tert-Butyl-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}serine;3-(TERT-BUTOXY)-2-{[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO}PROPANOIC ACID

Chemical Property of N-Fmoc-O-tert-butyl-DL-serine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 3.16E-14mmHg at 25°C
• Melting Point: 127-131 °C
• Refractive Index: 24 ° (C=1, AcOEt)
• Boiling Point: 578.6 °C at 760 mmHg
• PKA: 3.44±0.10(Predicted)
• Flash Point: 303.7 °C
• PSA: 84.86000
• Density: 1.216 g/cm³
• LogP: 4.18430
• Storage Temp.: 2-8°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 383.17327290
• Heavy Atom Count: 28
• Complexity: 536

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

Fmoc-Ser(tBu)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: Fmoc-Ser(tBu)-OH is an N-terminal protected reagent used in the peptide synthesis. Some of the reported examples are:Total synthesis of an antibiotic, daptomycin, by cyclization via a chemoselective serine ligation.Preparation of MUC1, a T-cell helper peptide, using iterative pentafluorophenyl ester-mediated fragment condensations.Linear solid-phase peptide synthesis of ubiquitin and diubiquitin.

Technology Process of N-Fmoc-O-tert-butyl-DL-serine

There total 17 articles about N-Fmoc-O-tert-butyl-DL-serine 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%

Fmoc-Ser(tBu)-OMe → Fmoc-Ser(tBu)-OH (71989-33-8)

Guidance literature:

With magnesium iodide; In tetrahydrofuran; at 120 ℃; for 1h; chemoselective reaction; Inert atmosphere; Microwave irradiation; Sealed tube;

DOI:10.1002/chem.201501799

Reference yield: 84.8%

N-Fmoc-L-Ser(t-But)-OEt → Fmoc-Ser(tBu)-OH (71989-33-8)

Guidance literature:

With aluminum (III) chloride; In ethyl acetate; Reflux;

Reference yield: 76.0%

(S)-3-tert-Butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester (129460-16-8) → Fmoc-Ser(tBu)-OH (71989-33-8) + N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5)

Guidance literature:

With silica gel; In toluene; for 1.25h; Heating;

DOI:10.1016/S0040-4039(01)00980-7

upstream raw materials:

(S)-O-tert-butylserine

9-fluorenylmethyl N-succinimidyl carbonate

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

O-tert-Butyl-L-serine Methyl Ester p-Toluenesulfonate

Downstream raw materials:

Fmoc-Ser(tBu)-Lys(Z)-OMe

O-tert-butyl-N^α-(fluoren-9-ylmethoxycarbonyl)-L-serine pentafluorophenyl ester

Refernces

• 1、 -. "Preparation method of fmoc-O-tert-butyl-L-serine". Paragraph 0005; 0024; 0028; 0029; 0034; 0035; 0039; 0040. . Retrieved 2019/02/17.
• 2、 Siciliano, Carlo,De Marco, Rosaria,Guidi, Ludovica Evelin,Spinella, Mariagiovanna,Liguori, Angelo. "A one-pot procedure for the preparation of N-9-fluorenylmethyloxycarbonyl- α-amino diazoketones from α-amino acids". . p. 10575 - 10582. Retrieved 2013/02/22.