n-Boc-d-homoserine tert-butyl ester

Base Information

• Chemical Name: n-Boc-d-homoserine tert-butyl ester
• CAS No.: 110207-49-3
• Molecular Formula: C₁₃H₂₅NO₅
• Molecular Weight: 275.345
• DSSTox Substance ID: DTXSID801157470
• Mol file: 110207-49-3.mol

Synonyms:110207-49-3;n-boc-d-homoserine tert-butyl ester;D-Homoserine, N-[(1,1-dimethylethoxy)carbonyl]-, 1,1-dimethylethyl ester;TERT-BUTYL (TERT-BUTOXYCARBONYL)-D-HOMOSERINATE;SCHEMBL6296123;WFSWHDJTFHDJFE-SECBINFHSA-N;DTXSID801157470;AT21843;CS-0435492;tert-butyl N-(tert-butoxycarbonyl)-D-homoserinate;(R)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate;N-[(1,1-Dimethylethoxy)carbonyl]-D-homoserine 1,1-dimethylethyl ester;tert-butyl (2R)-4-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate

Chemical Property of n-Boc-d-homoserine tert-butyl ester

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 275.17327290
• Heavy Atom Count: 19
• Complexity: 314

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(CCO)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)(C)OC(=O)[C@@H](CCO)NC(=O)OC(C)(C)C

Technology Process of n-Boc-d-homoserine tert-butyl ester

There total 1 articles about n-Boc-d-homoserine tert-butyl ester 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:

di-tert-butyl dicarbonate (24424-99-5) + N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + prenyl bromide (870-63-3) → tert-butyl D-N-(tert-butoxycarbonyl)homoserinate (110207-49-3) + N-(tert-butyloxycarbonyl)-(S)-homoserine tert-butyl ester (81323-58-2)

Guidance literature:

Multistep reaction. Title compound not separated from byproducts.;

DOI:10.1002/ejoc.200400063

Reference yield: 84.0%

4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (38250-16-7) + tert-butyl D-N-(tert-butoxycarbonyl)homoserinate (110207-49-3) → methyl <4--3-(tert-butoxycarbonyl)propoxy>benzoyl>formate (110207-50-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(00)83888-5

Reference yield:

tert-butyl D-N-(tert-butoxycarbonyl)homoserinate (110207-49-3) → di-tert-butyl N-(tert-butoxycarbonyl)nocardicin A (110269-45-9,110207-52-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / Et-OOC-N=N-COO-Et; PPh₃ / tetrahydrofuran / Ambient temperature

2: 86 percent / aq. NaOH / methanol / 0.25 h / 0 °C

3: 78 percent / i-BuOCOCl/2,6 lutidine / dimethylformamide; CH₂Cl₂ / 2 h

4: 79 percent / NH₂OH*HCl, 2,6-lutidine / ethanol / 9 h / Ambient temperature

With 2,6-dimethylpyridine; sodium hydroxide; hydroxylamine hydrochloride; triphenylphosphine; diethylazodicarboxylate; isobutyl chloroformate; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)83888-5

upstream raw materials:

di-tert-butyl dicarbonate

N-(diphenylmethylene)glycine tert-butyl ester

prenyl bromide

Downstream raw materials:

methyl <4--3-(tert-butoxycarbonyl)propoxy>benzoyl>formate

tert-butyl D-2-<(tert-butoxycarbonyl)amino>-4-bromobutyrate

<4--3-(tert-butoxycarbonyl)propoxy>benzoyl>formic acid

di-tert-butyl N-(tert-butoxycarbonyl)nocardicin D