Fmoc-D-threonine

Base Information

• Chemical Name: Fmoc-D-threonine
• CAS No.: 157355-81-2
• Molecular Formula: C19H19NO5
• Molecular Weight: 341.364
• Hs Code.: 29225090
• European Community (EC) Number: 857-384-5
• DSSTox Substance ID: DTXSID10426318
• Nikkaji Number: J933.029A
• Wikidata: Q72478770
• Mol file: 157355-81-2.mol

Synonyms:Fmoc-D-threonine;157355-81-2;Fmoc-D-Thr-OH;(2R,3S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxybutanoic acid;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-threonine;N-ALPHA-FMOC-D-THREONINE;(((9H-Fluoren-9-yl)methoxy)carbonyl)-D-threonine;D-Threonine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;(2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxybutanoic acid;N-Fmoc-D-threonine;MFCD00153365;(2R,3S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-hydroxybutanoic acid;N-Fmoc-D-Thr(OH);Fmoc-D-Thr-OH.nH2O;Fmoc-D-Thr-OH, AldrichCPR;DTXSID10426318;OYULCCKKLJPNPU-APPDUMDISA-N;AKOS015840856;CS-W011902;HY-W011186;AS-10558;D77728;EN300-650791;A883505;D-Threonine,N-[[1-(9H-fluoren-9-yl)ethoxy]carbonyl]-;(2R,3S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxybutanoicacid;(2R,3S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-HYDROXYBUTANOIC ACID

Chemical Property of Fmoc-D-threonine

Chemical Property:

• Vapor Pressure: 4.45E-15mmHg at 25°C
• Refractive Index: 15 ° (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:

≥98%,≥99%, ^*data from raw suppliers

N-Fmoc-D-threonine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

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-D-threonine is an N-Fmoc-protected form of D-Threonine (T405525). D-Threonine is the unnatural isomer of L-Threonine (T405500) and is known to inhibit growth and cell wall synthesis of Mycobacterium smegmatis. D-Threonine is also used as a synthetic intermediate for the production of chiral antibiotics.

Technology Process of Fmoc-D-threonine

There total 3 articles about Fmoc-D-threonine 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%

D-Threonine (632-20-2,134357-96-3,7013-32-3,82822-12-6) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → (((9H-fluoren-9-yl)methoxy)carbonyl)-D-threonine (157355-81-2)

Guidance literature:

With sodium carbonate; In 1,4-dioxane;

DOI:10.1016/0040-4039(94)85046-1

Reference yield:

2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxybutanoic acid → Fmoc-Thr-OH (73731-37-0) + (((9H-fluoren-9-yl)methoxy)carbonyl)-D-threonine (157355-81-2)

Guidance literature:

With chiral column based on 3,5-dimethylphenylcarbamoylated β-cyclodextrin combining cinchona alkaloid immobilized on silica gel; In methanol; formic acid; triethylamine; acetonitrile; at 25 ℃; Reagent/catalyst; enantioselective reaction; Resolution of racemate;

DOI:10.1002/chir.23237

Reference yield:

D-Threonine (632-20-2,134357-96-3,7013-32-3,82822-12-6) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (((9H-fluoren-9-yl)methoxy)carbonyl)-D-threonine (157355-81-2)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 - 20 ℃;

DOI:10.1021/ol100135a

upstream raw materials:

D-Threonine

(fluorenylmethoxy)carbonyl chloride

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

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、 Yu, Shun-Ming,Hong, Wen-Xu,Wu, Yuan,Zhong, Chun-Long,Yao, Zhu-Jun. "Total synthesis of chloptosin, a potent apoptosis-lnducing cyclopeptide". supporting information; experimental part. p. 1124 - 1127. Retrieved 2010/06/13.