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

Base Information

• Chemical Name: [(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-acetic acid
• CAS No.: 156774-22-0
• Molecular Formula: C₂₀H₃₂N₄O₆S₂
• Molecular Weight: 488.629
• Mol file: 156774-22-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about [(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-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: 95.0%

[(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-acetic acid methyl ester (156774-20-8) → [(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-acetic acid (156774-22-0)

Guidance literature:

With lithium hydroxide; In methanol; water; for 1h;

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) → [(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-acetic acid (156774-22-0)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 72 percent / NaH / tetrahydrofuran / 15 h / 0 - 20 °C

3: 95 percent / LiOH / H₂O; methanol / 1 h

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

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

Reference yield:

Boc(tosyl)arginine → [(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-acetic acid (156774-22-0)

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

4: 95 percent / LiOH / H₂O; methanol / 1 h

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

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

upstream raw materials:

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