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

Base Information

• Chemical Name: [(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-acetic acid methyl ester
• CAS No.: 156774-20-8
• Molecular Formula: C₂₁H₃₄N₄O₆S₂
• Molecular Weight: 502.656
• Mol file: 156774-20-8.mol

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

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

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 methyl ester

There total 3 articles about [(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-acetic acid methyl ester 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: 72.0%

potassium salt of methyl thioglycolate + Toluene-4-sulfonic acid (S)-5-({amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentyl ester (156774-19-5) → [(S)-5-({Amino-[(Z)-toluene-4-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentylsulfanyl]-acetic acid methyl ester (156774-20-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 15h;

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 methyl ester (156774-20-8)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; sodium hydride; In tetrahydrofuran; chloroform;

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 methyl ester (156774-20-8)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; borane-THF; sodium hydride; In tetrahydrofuran; chloroform;

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

upstream raw materials:

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

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

Downstream raw materials:

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

(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