Boc-D-Threonine

Base Information

• Chemical Name: Boc-D-Threonine
• CAS No.: 55674-67-4
• Molecular Formula: C₉H₁₇NO₅
• Molecular Weight: 219.238
• Hs Code.: 2924199090
• European Community (EC) Number: 834-870-5
• DSSTox Substance ID: DTXSID501257532
• Nikkaji Number: J1.042.452F
• Mol file: 55674-67-4.mol

Synonyms:Boc-D-Thr-OH;55674-67-4;Boc-D-Threonine;N-(tert-Butoxycarbonyl)-D-threonine;(2R,3S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxybutanoic acid;N-Boc-D-threonine;D-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-;N-ALPHA-TERT-BUTOXYCARBONYL-D-THREONINE;(2R,3s)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid;MFCD00037807;SCHEMBL1312767;(tert-Butoxycarbonyl)-D-threonine;LLHOYOCAAURYRL-NTSWFWBYSA-N;DTXSID501257532;86748-77-8;AKOS024258522;CS-W009516;HY-W008800;DS-15168;F10935;N-[(1,1-Dimethylethoxy)carbonyl]-D-threonine;EN300-1589311;A851291;(2R,3S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxybutanoicacid;(2R,3S)-2-(tert-butoxycarbonylamino)-3-hydroxybutanoic acid;(2R,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxybutanoic acid

Chemical Property of Boc-D-Threonine

Chemical Property:

• Vapor Pressure: 1.36E-07mmHg at 25°C
• Melting Point: 81 ºC
• Refractive Index: 9 ° (C=1, AcOH)
• Boiling Point: 387.1oC at 760 mmHg
• Flash Point: 187.9oC
• PSA: 95.86000
• Density: 1.202g/cm3
• LogP: 0.73600
• Storage Temp.: Store at RT.
• Water Solubility.: Slightly soluble in water.
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 219.11067264
• Heavy Atom Count: 15
• Complexity: 245

Purity/Quality:

min 98.0% ^*data from raw suppliers

Boc-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)OC(C)(C)C)O
• Isomeric SMILES: C[C@@H]([C@H](C(=O)O)NC(=O)OC(C)(C)C)O
• Uses: It is known to inhibit growth and cell wall synthesis of Mycobacterium smegmatis. Also used as a synthetic intermediate for the production of chiral antibiotics.

Technology Process of Boc-D-Threonine

There total 21 articles about Boc-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%

(2S,3S)-2-amino-3-hydroxybutanoic acid (28954-12-3,134357-96-3,7013-32-3,82822-12-6) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-butoxycarbonyl-L-allo-threonine (2592-18-9,23082-29-3,55674-67-4,85979-33-5,86748-77-8,23082-30-6)

Guidance literature:

In methanol; water; at 20 ℃; for 24h;

DOI:10.1039/C8OB01756E

Reference yield: 100.0%

D-Threonine (632-20-2,134357-96-3,7013-32-3,82822-12-6) + di-tert-butyl dicarbonate (24424-99-5) → (2R,3S)-2-tert-butoxycarbonylamino-3-hydroxybutyric acid (2592-18-9,23082-29-3,23082-30-6,55674-67-4,85979-33-5,86748-77-8)

Guidance literature:

With sodium hydroxide; In water; tert-butyl alcohol; at 20 ℃; for 23h;

DOI:10.1016/j.febslet.2013.07.016

Reference yield: 99.4%

di-tert-butyl dicarbonate (24424-99-5) + (2R,3S)-2-amino-3-hydroxybutanoic acid hydrochloride → (2R,3S)-2-tert-butoxycarbonylamino-3-hydroxybutyric acid (2592-18-9,23082-29-3,23082-30-6,55674-67-4,85979-33-5,86748-77-8)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; Cooling with ice;

upstream raw materials:

D-allo-threonine

di-tert-butyl dicarbonate

(2S,3S)-2-amino-3-hydroxybutanoic acid

N-(tert-butyloxycarbonyl) azide

Downstream raw materials:

Boc-aThr-(N^ε-Z-Lys-OCH3)

O-benzyl-α-N-t-BOC-D,L-allo-threonine hydroxamate

Boc-L-aThr-L-Phe-L-Pro-Thz-OMe

[(1S,2S)-2-Hydroxy-1-((R)-1-phenyl-ethylcarbamoyl)-propyl]-carbamic acid tert-butyl ester

Refernces

• 1、 Braun, Marie-Gabrielle,Burdick, Daniel J.,Castanedo, Georgette M.,Chen, Yi-Chen,Cheng, Yun-Xing,Cheong, Jonathan,Daniels, Blake,Deshmukh, Gauri,Fu, Yuhong,Garland, Keira,Gibbons, Paul,Gloor, Susan L.,Hanan, Emily J.,Hua, Rongbao,Kapadia, Sharookh B.,Labadie, Sharada,Liu, Xiongcai,Pantua, Homer,Pastor, Richard,Stivala, Craig,Xu, Min,Xu, Yiming,Zheng, Hao. "Optimization of globomycin analogs as novel gram-negative antibiotics". supporting information. . Retrieved 2020/08/13.
• 2、 Williams, Jade C.,Sheldon, Jessica R.,Imlay, Hunter D.,Dutter, Brendan F.,Draelos, Matthew M.,Skaar, Eric P.,Sulikowski, Gary A.. "Synthesis of the Siderophore Coelichelin and Its Utility as a Probe in the Study of Bacterial Metal Sensing and Response". supporting information. p. 679 - 682. Retrieved 2019/02/07.