(S)-2-Benzyloxycarbonylamino-1,4-bis(methanesulf

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-1,4-bis(methanesulf
• CAS No.: 176970-05-1
• Molecular Formula: C14H21NO8S2
• Molecular Weight: 395.455
• Mol file: 176970-05-1.mol

Synonyms:Carbamicacid, [3-[(methylsulfonyl)oxy]-1-[[(methylsulfonyl)oxy]methyl]propyl]-,phenylmethyl ester, (S)-;(S)-2-Benzyloxycarbonylamino-1,4-bis(methanesulfonyloxy)butane;

Chemical Property of (S)-2-Benzyloxycarbonylamino-1,4-bis(methanesulf

Chemical Property:

• Boiling Point: 656.961 °C at 760 mmHg
• PKA: 11.06±0.46(Predicted)
• Flash Point: 351.118 °C
• PSA: 141.83000
• Density: 1.369 g/cm³
• LogP: 3.17640

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-Benzyloxycarbonylamino-1,4-bis(methanesulf

There total 4 articles about (S)-2-Benzyloxycarbonylamino-1,4-bis(methanesulf 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: 85.0%

methanesulfonyl chloride (124-63-0) + [(1S)-3-hydroxy-1-(hydroxymethyl)propyl]carbamic acid phenylmethyl ester (118219-23-1) → (S)-2-(((benzyloxy)carbonyl)amino)butane-1,4-diyl dimethanesulfonate (176970-05-1)

Guidance literature:

With triethylamine; In ethyl acetate; at 5 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1080/00397911.2018.1509093

Reference yield:

dimethyl (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate (35909-93-4) → (S)-2-(((benzyloxy)carbonyl)amino)butane-1,4-diyl dimethanesulfonate (176970-05-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 11.9 g / NaBH₄ / tetrahydrofuran; methanol / 45 - 55 °C

2: 16.9 g / Et₃N / ethyl acetate / 1 h / -20 - -5 °C

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran; methanol; ethyl acetate;

Reference yield:

N-Cbz-L-Asp (1152-61-0) → (S)-2-(((benzyloxy)carbonyl)amino)butane-1,4-diyl dimethanesulfonate (176970-05-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 33.2 g / 1N HCl / Ambient temperature

2: 11.9 g / NaBH₄ / tetrahydrofuran; methanol / 45 - 55 °C

3: 16.9 g / Et₃N / ethyl acetate / 1 h / -20 - -5 °C

With hydrogenchloride; sodium tetrahydroborate; triethylamine; In tetrahydrofuran; methanol; ethyl acetate;

upstream raw materials:

methanesulfonyl chloride

[(1S)-3-hydroxy-1-(hydroxymethyl)propyl]carbamic acid phenylmethyl ester

dimethyl (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate

N-Cbz-L-Asp

Downstream raw materials:

(S)-benzyl pyrrolidin-3-ylcarbamate

(S)-1-allyl-3-(benzyloxycarbonylamino)pyrrolidine

N-propyl-3-(benzyloxycarbonylamino)pyrrolidine

Refernces

• 1、 Tomori, Hiroshi,Shibutani, Kuniko,Ogura, Katsuyuki. "Practical synthesis of (S)-3-(p-nitrobenzyloxy-carbonylamino)pyrrolidine and its related compounds from L-aspartic acid". . p. 213 - 225. Retrieved 2007/10/03.