(S)-tert-Butyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate

Base Information

• Chemical Name: (S)-tert-Butyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate
• CAS No.: 59859-77-7
• Molecular Formula: C15H21NO5
• Molecular Weight: 295.335
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID30456733
• Nikkaji Number: J938.145G
• Wikidata: Q82279293
• Mol file: 59859-77-7.mol

Synonyms:59859-77-7;(S)-tert-Butyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate;tert-Butyl ((benzyloxy)carbonyl)-L-serinate;tert-butyl (2S)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoate;TERT-BUTYL (2S)-2-{[(BENZYLOXY)CARBONYL]AMINO}-3-HYDROXYPROPANOATE;N-Cbz-O-t-butyl-L-serine;SCHEMBL2677162;DTXSID30456733;(S)-tert-Butyl2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate;n-benzyloxycarbonyl-l-serine tert-butyl ester;N-(Benzyloxycarbonyl)-L-serine tert-butyl ester;EN300-12575465;tert-Butyl 2-([(benzyloxy)carbonyl]amino)-3-hydroxypropanoate #

Chemical Property of (S)-tert-Butyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate

Chemical Property:

• Melting Point: 87.5 °C
• Boiling Point: 458.8±45.0 °C(Predicted)
• PKA: 10.49±0.46(Predicted)
• PSA: 88.35000
• Density: 1.174±0.06 g/cm3(Predicted)
• LogP: 1.81980
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 295.14197277
• Heavy Atom Count: 21
• Complexity: 345

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-tert-Butyl2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(CO)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)[C@H](CO)NC(=O)OCC1=CC=CC=C1

Technology Process of (S)-tert-Butyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate

There total 12 articles about (S)-tert-Butyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate 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: 91.0%

N-[(phenylmethoxy)carbonyl]-L-serine ethanoate 1,1-dimethylethyl ester (289655-98-7) → 2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester (59859-77-7)

Guidance literature:

With diazene; In ethanol; at 0 - 20 ℃;

DOI:10.1016/S0040-4020(00)00280-5

Reference yield: 90.0%

tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) + N-(benzyloxycarbonyl)-L-serine (1145-80-8) → 2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester (59859-77-7)

Guidance literature:

In cyclohexane; ethyl acetate; at 22 ℃; for 16h;

DOI:10.1021/acs.orglett.7b03967

Reference yield: 88.0%

t-butyl bromide (507-19-7) + N-(benzyloxycarbonyl)-L-serine (1145-80-8) → 2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester (59859-77-7)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In acetonitrile; at 48 ℃; for 24h;

DOI:10.1016/j.tetasy.2005.11.019

upstream raw materials:

O-acetyl-N-benzyloxycarbonyl-serine

t-butyl bromide

N-(benzyloxycarbonyl)-L-serine

tert-butyl alcohol

Downstream raw materials:

tert-butyl 2-amino-3-hydroxypropanoate

N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-serine tert-butyl ester

N-benzyloxycarbonyl-O-<3,4,6-tri-O-acetyl-2-N-(2,2,2-trichloroethyloxycarbonyl)-amino-2-deoxy-β-D-glucopyranosyl>-serine tert-butyl ester

O^ω-<4-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>butyryl>-N^α-<(phenylmethoxy)carbonyl>-L-serine, 1,1-dimethylethyl ester