N-(tert-Butoxycarbonyl)-D-threonine

Base Information

• Chemical Name: N-(tert-Butoxycarbonyl)-D-threonine
• CAS No.: 85979-33-5
• Molecular Formula: C₉H₁₇NO₅
• Molecular Weight: 219.238
• European Community (EC) Number: 860-514-3
• Nikkaji Number: J731.196F
• Mol file: 85979-33-5.mol

Synonyms:85979-33-5;N-(tert-Butoxycarbonyl)-D-threonine;D-Allothreonine, N-[(1,1-dimethylethoxy)carbonyl]- (9CI);(2R,3R)-2-((tert-Butoxycarbonyl)amino)-3-hydroxybutanoic acid;N-[(1,1-DIMETHYLETHOXY)CARBONYL]-D-ALLOTHREONINE;(2R,3R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid;N-Boc-D-threonine;N-Boc-D-allo-threonine;BOC-D-ALLOTHREONINE;SCHEMBL1311851;LLHOYOCAAURYRL-PHDIDXHHSA-N;AKOS015923035;AT21343;N-(tert-Butoxycarbonyl)-D-allothreonine;N-(tert-butoxycarbonyl)-D-allo-threonine;B2990;CS-0343531;EN300-3222138;N-{[(1,1-dimethylethyl)oxy]carbonyl}-D-allothreonine;(2R,3R)-2-((tert-Butoxycarbonyl)amino)-3-hydroxybutanoicacid;(2R,3R)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxybutanoic acid

Chemical Property of N-(tert-Butoxycarbonyl)-D-threonine

Chemical Property:

• PSA: 95.86000
• LogP: 0.73600
• 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:

99% ^*data from raw 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

Technology Process of N-(tert-Butoxycarbonyl)-D-threonine

There total 21 articles about N-(tert-Butoxycarbonyl)-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:

C₁₉H₂₈N₂O₆

(2R,3S)-methyl 2-<(tert-butoxycarbonyl)amino>-3-hydroxybutanoate

((2R,3S)-1-Benzyloxy-2-methyl-4-oxo-azetidin-3-yl)-carbamic acid tert-butyl ester

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

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.