2-[(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-benzoic acid

Base Information

• Chemical Name: 2-[(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-benzoic acid
• CAS No.: 156774-23-1
• Molecular Formula: C₂₅H₃₄N₄O₆S₂
• Molecular Weight: 550.7
• Mol file: 156774-23-1.mol

Synonyms:2-[(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-benzoic acid

Chemical Property of 2-[(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-benzoic acid

There total 4 articles about 2-[(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-benzoic 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: 83.0%

2-[(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-benzoic acid methyl ester (156774-21-9) → 2-[(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-benzoic acid (156774-23-1)

Guidance literature:

With lithium hydroxide; In methanol; water; for 18h; Ambient temperature;

DOI:10.1016/S0040-4039(00)76226-5

Reference yield:

[(S)-4-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-1-hydroxymethyl-butyl]-carbamic acid tert-butyl ester (129397-84-8) → 2-[(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-benzoic acid (156774-23-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / pyridine / CHCl₃ / 1 h / Ambient temperature

2: 95 percent / NaH / tetrahydrofuran / 15 h / 0 - 20 °C

3: 83 percent / LiOH / H₂O; methanol / 18 h / Ambient temperature

With pyridine; lithium hydroxide; sodium hydride; In tetrahydrofuran; methanol; chloroform; water;

DOI:10.1016/S0040-4039(00)76226-5

Reference yield:

Boc(tosyl)arginine → 2-[(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-benzoic acid (156774-23-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / BH₃*THF / tetrahydrofuran / 3 h / -70 - 10 °C

2: 78 percent / pyridine / CHCl₃ / 1 h / Ambient temperature

3: 95 percent / NaH / tetrahydrofuran / 15 h / 0 - 20 °C

4: 83 percent / LiOH / H₂O; methanol / 18 h / Ambient temperature

With pyridine; lithium hydroxide; borane-THF; sodium hydride; In tetrahydrofuran; methanol; chloroform; water;

DOI:10.1016/S0040-4039(00)76226-5

upstream raw materials:

2-[(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-benzoic acid methyl ester

[(S)-4-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-1-hydroxymethyl-butyl]-carbamic acid tert-butyl ester

Toluene-4-sulfonic acid (S)-5-({amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentyl ester

Downstream raw materials:

(S)-2-{2-[(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-benzoylamino}-succinic acid 4-cyclohexyl ester 1-methyl ester