N-Cbz-S-4-Hydroxyphenylglycine

Base Information

• Chemical Name: N-Cbz-S-4-Hydroxyphenylglycine
• CAS No.: 26787-76-8
• Molecular Formula: C16H15NO5
• Molecular Weight: 301.294
• European Community (EC) Number: 846-159-7
• DSSTox Substance ID: DTXSID301161004
• Mol file: 26787-76-8.mol

Synonyms:N-Cbz-S-4-Hydroxyphenylglycine;26787-76-8;(2S)-2-(4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)acetic acid;(2S)-2-{[(benzyloxy)carbonyl]amino}-2-(4-hydroxyphenyl)acetic acid;(2S)-2-([(BENZYLOXY)CARBONYL]AMINO)-2-(4-HYDROXYPHENYL)ACETIC ACID;SCHEMBL17765000;DTXSID301161004;(alphaS)-4-Hydroxy-alpha-[[(phenylmethoxy)carbonyl]amino]benzeneacetic acid;AKOS037645343;AS-60284;D86762;EN300-6488767;(2S)-{[(Benzyloxy)carbonyl]amino}(4-hydroxyphenyl)acetic acid

Chemical Property of N-Cbz-S-4-Hydroxyphenylglycine

Chemical Property:

• Boiling Point: 552℃
• PKA: 3.69±0.10(Predicted)
• Flash Point: 288℃
• PSA: 95.86000
• Density: 1.356
• LogP: 2.83520
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 301.09502258
• Heavy Atom Count: 22
• Complexity: 373

Purity/Quality:

98%Min ^*data from raw suppliers

N-Cbz-S-4-Hydroxyphenylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(C2=CC=C(C=C2)O)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](C2=CC=C(C=C2)O)C(=O)O

Technology Process of N-Cbz-S-4-Hydroxyphenylglycine

There total 2 articles about N-Cbz-S-4-Hydroxyphenylglycine 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%

(S)-hydroxyphenylglycine (32462-30-9) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-N-benzyloxycarbonyl-4-hydroxyphenylglycine (26787-76-8)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 25 ℃; for 1.5h;

DOI:10.1002/anie.201103315

Reference yield:

(S)-Benzyloxycarbonylamino-(4-hydroxy-phenyl)-acetic acid 4-nitro-benzyl ester → (S)-N-benzyloxycarbonyl-4-hydroxyphenylglycine (26787-76-8)

Guidance literature:

With antibody 7G₁₂; Tris buffer; water; In dimethyl sulfoxide; at 25 ℃; Rate constant;

DOI:10.1021/ja952220w

Reference yield: 63.0%

benzyl bromide (100-39-0) + (S)-N-benzyloxycarbonyl-4-hydroxyphenylglycine (26787-76-8) → Cbz-L-Hpg-OBn (1352788-59-0)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 25 ℃; for 15h;

DOI:10.1002/anie.201103315

upstream raw materials:

(S)-hydroxyphenylglycine

benzyl chloroformate

Downstream raw materials:

(S)-N-benzyloxycarbonyl-4-tert-butoxyphenylglycine tert-butyl ester

N-benzyloxycarbonyl-L-(p-hydroxyphenyl)glycine-N-methylamide

(R)-N⁴-Benzyloxy-N¹-[(S)-(4-hydroxy-phenyl)-methylcarbamoyl-methyl]-2-isobutyl-succinamide

(S)-4-tert-butoxyphenylglycine tert-butyl ester hydrochloride