Fmoc-D-Thr(tBu)-OH

Base Information

• Chemical Name: Fmoc-D-Thr(tBu)-OH
• CAS No.: 138797-71-4
• Molecular Formula: C₂₃H₂₇NO₅
• Molecular Weight: 397.471
• Hs Code.: 2924 29 70
• European Community (EC) Number: 882-206-8
• UNII: S7MR4J6PSM
• DSSTox Substance ID: DTXSID80427357
• Wikidata: Q72478933
• Mol file: 138797-71-4.mol

Synonyms:Fmoc-D-Thr(tBu)-OH;138797-71-4;Fmoc-O-tert-butyl-D-threonine;(2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]butanoic acid;(2S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid;D-Threonine, O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;(2R,3S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid;Fmoc-O-tert.butyl-D-threonine;MFCD00080292;S7MR4J6PSM;SCHEMBL3310968;DTXSID80427357;N-Fmoc-O-tert-butyl-D-threonine;AKOS015892639;AM82251;CS-W000843;HY-W000843;AS-19663;PD196374;F1128;EN300-95049;Fmoc-D-Thr(tBu)-OH, >=98.0% (TLC);H10902;M03393;J-007178;Z1270111722;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-tert-butyl-D-threonine;N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-t-butyl-D-threonine;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyl)-D-threonine;O-(1,1-Dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-threonine;(2R,3S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)butanoicacid;(2R,3S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-tert-butoxybutanoic acid;(2R,3S)-3-(tert-butoxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid

Chemical Property of Fmoc-D-Thr(tBu)-OH

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.24E-14mmHg at 25°C
• Melting Point: ~130 °C
• Refractive Index: 1.568
• Boiling Point: 581.7 °C at 760 mmHg
• PKA: 3.42±0.10(Predicted)
• Flash Point: 305.6 °C
• PSA: 84.86000
• Density: 1.197 g/cm³
• LogP: 4.57280
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 397.18892296
• Heavy Atom Count: 29
• Complexity: 564

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-O-tert-butyl-D-threonine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OC(C)(C)C
• Isomeric SMILES: C[C@@H]([C@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OC(C)(C)C
• Uses: O-(1,1-Dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-threonine is a reagent used in developing CNS active opioid glycopeptides which are potential drug candidates that penetrate the blood-brain barrier to produce potent central effects.

Technology Process of Fmoc-D-Thr(tBu)-OH

There total 23 articles about Fmoc-D-Thr(tBu)-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%

Fmoc?(R)?allo?Thr(tBu)?OH → Nα-(9-Fluorenylmethoxycarbonyl)-D-allothreonine t-butyl ether (170643-02-4,138797-71-4)

Guidance literature:

With palladium on activated charcoal; hydrogen; at 20 ℃;

DOI:10.1007/s00726-018-2677-5

Reference yield: 84.0%

(2R,3R)-3-tert-Butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester → Nα-(9-Fluorenylmethoxycarbonyl)-D-allothreonine t-butyl ether (170643-02-4,138797-71-4)

Guidance literature:

With zinc; In acetic acid;

DOI:10.1016/00404-0399(50)0992L-

Reference yield: 70.0%

(O-tert-butyl)-L-threonine (4378-13-6,201353-89-1) + 9-fluorenylmethyl N-succinimidyl carbonate (102774-86-7) → Fmoc-Thr(tBu)-OH (71989-35-0,138797-71-4)

Guidance literature:

With triethylamine; In water; acetonitrile; for 1h;

upstream raw materials:

(O-tert-butyl)-L-threonine

9-fluorenylmethyl N-succinimidyl carbonate

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

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

Refernces

• 1、 -. "A Fmoc - Thr (tBu) - OH preparation method (by machine translation)". Paragraph 0031-0038. . Retrieved 2019/02/04.
• 2、 Tokairin, Yoshinori,Soloshonok, Vadim A.,Moriwaki, Hiroki,Konno, Hiroyuki. "Asymmetric synthesis of (2S,3S)-3-Me-glutamine and (R)-allo-threonine derivatives proper for solid-phase peptide coupling". . p. 419 - 432. Retrieved 2018/11/27.