Fmoc-Thr-OH

Base Information

• Chemical Name: Fmoc-Thr-OH
• CAS No.: 73731-37-0
• Molecular Formula: C19H19NO5
• Molecular Weight: 341.364
• Hs Code.: 29242990
• European Community (EC) Number: 630-403-2
• Nikkaji Number: J1.365.142F
• Mol file: 73731-37-0.mol

Synonyms:Fmoc-Thr-OH;73731-37-0;FMOC-L-THREONINE;(2S,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxybutanoic acid;2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butanoic acid;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-threonine;MFCD00077072;Fmoc-Thr-OH monohydrate;(2S,3R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-hydroxybutanoic acid;N-Fmoc-L-threonine;Fmoc-Thr-OH.nH2O;SCHEMBL2551441;OYULCCKKLJPNPU-DIFFPNOSSA-N;AKOS015837088;AKOS015895366;CS-W009412;HY-W008696;N-(9-Fluorenylmethoxycarbonyl)threonine;AS-50298;AM20041096;F0455;EN300-81295;M03388;Nalpha-(9-Fluorenylmethoxycarbonyl)-L-threonine;O11819;N-(9H-Fluorene-9-ylmethoxycarbonyl)-L-threonine;(((9H-fluoren-9-yl)methoxy)carbonyl)-L-threonine;A837911;Z1227754900;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-THREONINE;(2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxidanyl-butanoic acid;(2S,3R)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-HYDROXYBUTANOIC ACID;(2S,3R)-2-[[9H-fluoren-9-ylmethoxy(oxo)methyl]amino]-3-hydroxybutanoic acid

Chemical Property of Fmoc-Thr-OH

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 4.45E-15mmHg at 25°C
• Melting Point: 115°C (dec.)
• Refractive Index: -15.5 ° (C=1, DMF)
• Boiling Point: 596.5 °C at 760 mmHg
• PKA: 3.49±0.10(Predicted)
• Flash Point: 314.6 °C
• PSA: 95.86000
• Density: 1.327 g/cm³
• LogP: 2.75000
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 341.12632271
• Heavy Atom Count: 25
• Complexity: 474

Purity/Quality:

99% ^*data from raw suppliers

N-Fmoc-L-threonine ^*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: CC(C(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)O
• Isomeric SMILES: C[C@H]([C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)O
• Uses: N-Fmoc-L-threonine is an N-Fmoc-protected form of L-Threonine (T405500). L-Threonine is an essential amino acid that is commonly used as a feed and food additive. L-Threonine is produced in mass quantities by mutant Escherichia coli strains for research and food nutrition purposes. L-Threonine can be naturally found in fish and poultry, and is incorporated in some important proteins in the human body (such as hemoglobin and insulin).

Technology Process of Fmoc-Thr-OH

There total 22 articles about Fmoc-Thr-OH 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-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-Thr-OH (73731-37-0)

Guidance literature:

With sodium hydrogencarbonate;

DOI:10.1002/ejoc.201100304

Reference yield: 100.0%

Fmoc-Thr(tBu)-OH (71989-35-0,138797-71-4) → Fmoc-Thr-OH (73731-37-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/ejoc.201901459

Reference yield: 96.0%

(2R,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butane-1,3-diol (176380-53-3,252049-02-8) → Fmoc-Thr-OH (73731-37-0)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; disodium hydrogenphosphate; potassium dihydrogenphosphate; sodium hypochlorite; sodium chlorite; In acetonitrile; at 45 ℃; for 12h;

DOI:10.1021/jo015844v

upstream raw materials:

L-threonine

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

(9-fluorenyl)methyl pentafluorophenyl carbonate

Fmoc-O-trityl-l-threonine

Downstream raw materials:

(2S,3R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyric acid 3-methyl-oxetan-3-ylmethyl ester

(2S,3R)-N'-(tert-butoxycarbonyl)-2-(fluoren-9-ylmethoxycarbonylamino)-3-hydroxybutyrohydrazide

(2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyric acid benzhydryl ester

ester p-nitrophenolique de la N-(fluorenylmethyloxycarbonyl)-L-threonine

Refernces

• 1、 Zhu, Lunan,Zhu, Junchen,Sun, Xiaotong,Wu, Yaling,Wang, Huiying,Cheng, Lingping,Shen, Jiawei,Ke, Yanxiong. "Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety". . p. 1080 - 1090. Retrieved 2020/05/25.
• 2、 Stra?burger, David,Glaffig, Markus,Stergiou, Natascha,Bialas, Sabrina,Besenius, Pol,Schmitt, Edgar,Kunz, Horst. "Synthetic MUC1 antitumor vaccine with incorporated 2,3-sialyl-T carbohydrate antigen inducing strong immune responses with isotype specificity". . p. 1142 - 1146. Retrieved 2018/10/21.