N-(tert-Butoxycarbonyl)-L-serine

Base Information

• Chemical Name: N-(tert-Butoxycarbonyl)-L-serine
• CAS No.: 3262-72-4
• Molecular Formula: C8H15NO5
• Molecular Weight: 205.211
• Hs Code.: 29241990
• European Community (EC) Number: 221-867-3
• DSSTox Substance ID: DTXSID601317842
• Nikkaji Number: J245.635D
• Wikidata: Q76009742
• ChEMBL ID: CHEMBL438330
• Mol file: 3262-72-4.mol

Synonyms:3262-72-4;Boc-Ser-OH;Boc-L-serine;N-Boc-L-serine;N-(tert-Butoxycarbonyl)-L-serine;(S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxypropanoic acid;N-Boc-serine;serine, N-[(1,1-dimethylethoxy)carbonyl]-;MFCD00037243;N-T-BUTOXYCARBONYL-L-SERINE;N-(tert-butoxycarbonyl)serine;(2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;EINECS 221-867-3;Boc-L-Ser-OH;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropanoic acid;(S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-HYDROXYPROPANOIC ACID;Boc-Serine;(2S)-2-(tert-Butoxycarbonylamino)-3-hydroxypropanoic acid;N-[tert-butoxycarbonyl]-L-serine;BOC-L-SER;(S)-N-BOC-SERINE;(2S)-2-[(tert-Butoxycarbonyl)amino]-3-hydroxypropanoic acid;BocSer;Boc serine;N-BocSerine;Boc-Ser;t-butyloxycarbonylserine;N-tert-butoxycarbonylserine;t-butyloxycarbonyl-L-serine;tert-butoxycarbonyl L-serine;tert-butoxycarbonyl-L-serine;N-t-butyloxycarbonyl-L-serine;SCHEMBL315980;N-(t-butoxycarbonyl)-L-serine;N-tert-butoxycarbonyl L-serine;(tert-Butoxycarbonyl)-L-serine;CHEMBL438330;Nalpha-t-butoxycarbonyl-L-serine;DTXSID601317842;N-(tert-butoxy-carbonyl)-L-serine;STR04011;AKOS010367742;AKOS015924243;Boc-Ser-OH, >=99.0% (T);CS-W015379;HY-W014663;NSC 164056;AC-17115;BP-11371;BP-31211;(S)-N-(1,1-dimethylethoxy)carbonylserine;N-ALPHA-T-BUTYLOXYCARBONYL-L-SERINE;(S)-2-(BOC-amino)-3-hydroxypropanoic acid;AM20090478;B1637;EN300-97162;L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-;M03318;N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-serine;AS-813/43499830;N-[(1,1-DIMETHYLETHOXY)CARBONYL]-L-SERINE;(2S)-3-hydroxy-2-t-butoxycarbonylaminopropanoic acid;(S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionic acid;(S)-2-tert-butoxycarbonylamino-3-hydroxypropionic acid;F1905-7614;(2S)-3-hydroxy-2-tert-butoxycarbonylamino-propionic acid

Chemical Property of N-(tert-Butoxycarbonyl)-L-serine

Chemical Property:

• Appearance/Colour: white to light brown powder
• Vapor Pressure: 1.61E-07mmHg at 25°C
• Melting Point: 91 °C (dec.)(lit.)
• Refractive Index: -4 ° (C=1, AcOH)
• Boiling Point: 385.1 °C at 760 mmHg
• PKA: 3.62±0.10(Predicted)
• Flash Point: 186.7 °C
• PSA: 95.86000
• Density: 1.24 g/cm³
• LogP: 0.34750
• Storage Temp.: 2-8°C
• Water Solubility.: almost transparency
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 205.09502258
• Heavy Atom Count: 14
• Complexity: 220

Purity/Quality:

≥98%, ^*data from raw suppliers

Boc-Ser ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CO)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O
• Uses: Boc-Ser-OH may be used in the synthesis of the following:2-(N-Fmoc)-3-(N-Boc-N-methoxy)-diaminopropanoic acid (Fmoc: 9-fluorenylmethoxycarbonyl; Boc: t-butyloxycarbonyl)Boc-Ser-Leu-OMecyclic peptide synthesisbenzylsulfonyl-D-Ser-Ser-4-amidinobenzylamide

Technology Process of N-(tert-Butoxycarbonyl)-L-serine

There total 32 articles about N-(tert-Butoxycarbonyl)-L-serine 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-Serine (312-84-5,83245-15-2) + di-tert-butyl dicarbonate (24424-99-5) → (R)-N-tert-butoxycarbonyl serine (3262-72-4,3850-40-6,6368-20-3,90582-28-8,84311-18-2)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 0 - 25 ℃; for 2h;

DOI:10.1021/ja00097a072

Reference yield: 100.0%

L-serin (56-45-1,83245-15-2) + di-tert-butyl dicarbonate (24424-99-5) → (S)-N-(tert-butoxycarbonyl)serine (3262-72-4)

Guidance literature:

DOI:10.3987/com-00-9014

Reference yield: 100.0%

BOC-O-benzyl-L-serine (23680-31-1) → (S)-N-(tert-butoxycarbonyl)serine (3262-72-4)

Guidance literature:

With palladium on carbon; In ethanol; cyclohexane; for 16h; Reflux;

DOI:10.1021/op7000172

upstream raw materials:

D-Serine

di-tert-butyl dicarbonate

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

(2R)-2-amino-3-hydroxypropanoic acid hydrochloride

Downstream raw materials:

N-(benzyloxy-2 phenyl) <(tert.butoxycarbonyl) amino>-2 hydroxy-3 propionamide (2-S)

Boc-D-Ser-D-Ala-OBzl

(S)-2-((R)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-hex-5-enoic acid benzyl ester

N-(benzyloxy-4 phenyl) <(tert.butoxycarbonyl) amino>-2 hydroxy-3 propionamide (2-S)

Refernces

• 1、 Ciufolini, Marco A.,Swaminathan, Shankar. "SYNTHESIS OF A MODEL DEPSIPEPTIDE SEGMENT OF LUZOPEPTINS (BBM 928), POTENT ANTITUMOR AND ANTIRETROVIRAL ANTIBIOTICS". . p. 3027 - 3028. Retrieved 1989.
• 2、 -. "PRODRUGS OF ABIRATERONE". Page/Page column 20-21. . Retrieved 2021/05/29.
• 3、 Fink, Julian,Schumacher, Fabian,Schlegel, Jan,Stenzel, Philipp,Wigger, Dominik,Sauer, Markus,Kleuser, Burkhard,Seibel, Jürgen. "Azidosphinganine enables metabolic labeling and detection of sphingolipidde novosynthesis". supporting information. p. 2203 - 2212. Retrieved 2021/03/24.