({(S)-2-[(S)-2-(5-Dimethylamino-naphthalene-1-sulfonylamino)-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-butyryl}-hydroxy-amino)-acetic acid

Base Information

• Chemical Name: ({(S)-2-[(S)-2-(5-Dimethylamino-naphthalene-1-sulfonylamino)-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-butyryl}-hydroxy-amino)-acetic acid
• CAS No.: 119880-80-7
• Molecular Formula: C₂₈H₃₄N₄O₈S
• Molecular Weight: 586.666
• Mol file: 119880-80-7.mol

Synonyms:({(S)-2-[(S)-2-(5-Dimethylamino-naphthalene-1-sulfonylamino)-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-butyryl}-hydroxy-amino)-acetic acid

Chemical Property of ({(S)-2-[(S)-2-(5-Dimethylamino-naphthalene-1-sulfonylamino)-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-butyryl}-hydroxy-amino)-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ({(S)-2-[(S)-2-(5-Dimethylamino-naphthalene-1-sulfonylamino)-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-butyryl}-hydroxy-amino)-acetic acid

There total 6 articles about ({(S)-2-[(S)-2-(5-Dimethylamino-naphthalene-1-sulfonylamino)-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-butyryl}-hydroxy-amino)-acetic acid 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:

5-(dimethylamino)naphth-1-ylsulfonyl chloride (605-65-2) → ({(S)-2-[(S)-2-(5-Dimethylamino-naphthalene-1-sulfonylamino)-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-butyryl}-hydroxy-amino)-acetic acid (119880-80-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / NaHCO₃ / acetone; H₂O

2: 100 percent / (i-PrN)2C, (i-Pr)2EtN / butan-1-ol; tetrahydrofuran

3: 100 percent / Et₃N / methanol; H₂O / 50 °C

4: 1.) i-BuOCOCl, (i-Pr)2EtN / 1.) CH₂Cl₂, 0 deg C, 2.) 0 deg C -> room temp.

5: B(OTf)3, TFA

With tris(trifluoromethanesulfonyloxy)boron; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; diisopropyl-carbodiimide; isobutyl chloroformate; In tetrahydrofuran; methanol; water; acetone; butan-1-ol;

DOI:10.1021/ja00187a088

Reference yield:

O-t-Butyl-L-tyrosine (4727-00-8,18822-59-8,186698-58-8) → ({(S)-2-[(S)-2-(5-Dimethylamino-naphthalene-1-sulfonylamino)-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-butyryl}-hydroxy-amino)-acetic acid (119880-80-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / NaHCO₃ / acetone; H₂O

2: 100 percent / (i-PrN)2C, (i-Pr)2EtN / butan-1-ol; tetrahydrofuran

3: 100 percent / Et₃N / methanol; H₂O / 50 °C

4: 1.) i-BuOCOCl, (i-Pr)2EtN / 1.) CH₂Cl₂, 0 deg C, 2.) 0 deg C -> room temp.

5: B(OTf)3, TFA

With tris(trifluoromethanesulfonyloxy)boron; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; diisopropyl-carbodiimide; isobutyl chloroformate; In tetrahydrofuran; methanol; water; acetone; butan-1-ol;

DOI:10.1021/ja00187a088

Reference yield:

O-tert-butyl-N-dansyltyrosine (119880-76-1) → ({(S)-2-[(S)-2-(5-Dimethylamino-naphthalene-1-sulfonylamino)-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-butyryl}-hydroxy-amino)-acetic acid (119880-80-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / (i-PrN)2C, (i-Pr)2EtN / butan-1-ol; tetrahydrofuran

2: 100 percent / Et₃N / methanol; H₂O / 50 °C

3: 1.) i-BuOCOCl, (i-Pr)2EtN / 1.) CH₂Cl₂, 0 deg C, 2.) 0 deg C -> room temp.

4: B(OTf)3, TFA

With tris(trifluoromethanesulfonyloxy)boron; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; diisopropyl-carbodiimide; isobutyl chloroformate; In tetrahydrofuran; methanol; water; butan-1-ol;

DOI:10.1021/ja00187a088

upstream raw materials:

(Benzyloxy-{(S)-2-[(S)-3-(4-tert-butoxy-phenyl)-2-(5-dimethylamino-naphthalene-1-sulfonylamino)-propionylamino]-3-methyl-butyryl}-amino)-acetic acid 4-methoxy-benzyl ester

5-(dimethylamino)naphth-1-ylsulfonyl chloride

O-t-Butyl-L-tyrosine

O-tert-butyl-N-dansyltyrosine