(2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[N-tert-butoxycarbonyl-1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine

Base Information

• Chemical Name: (2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[N-tert-butoxycarbonyl-1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine
• CAS No.: 782496-47-3
• Molecular Formula: C₅₁H₆₉N₃O₇SSi
• Molecular Weight: 896.276
• Mol file: 782496-47-3.mol

Synonyms:(2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[N-tert-butoxycarbonyl-1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine

Chemical Property of (2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[N-tert-butoxycarbonyl-1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[N-tert-butoxycarbonyl-1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine

There total 3 articles about (2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[N-tert-butoxycarbonyl-1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine 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: 69.0%

(2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine (782496-46-2) + di-tert-butyl dicarbonate (24424-99-5) → (2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[N-tert-butoxycarbonyl-1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine (782496-47-3)

Guidance literature:

In tetrahydrofuran; water; at 60 ℃; for 24h; pH=10;

DOI:10.1002/chem.200400181

Reference yield:

(2S/R,4R,7R,2'S,5'S,1''S)-4-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-7-[1''-N''-benzyl-(p-tolylsulfonyl)amino]-ethyl-2-oxo-1,3-dioxathiepane → (2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[N-tert-butoxycarbonyl-1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine (782496-47-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 98 percent / aq. NaIO₄ / RuCl₃ / CCl₄; acetonitrile / 0.33 h / 0 °C

2.1: tetrabutylammonium azide / tetrahydrofuran / 36 h / 35 °C

2.2: H₂SO₄ / tetrahydrofuran / 8 h / pH 1 - 2

2.3: 330 mg / MsCl; Et₃N / CH₂Cl₂ / 1 h / -40 - -15 °C

3.1: 69 percent / tetrahydrofuran; H₂O / 24 h / 60 °C / pH 10

With sodium periodate; tetrabutylammoniun azide; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; water; acetonitrile;

DOI:10.1002/chem.200400181

Reference yield:

(2S/R,4R,7R,2'S,5'S,1''S)-4-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-7-[1''-N''-benzyl-(p-tolylsulfonyl)amino]-ethyl-2,2-dioxo-1,3-dioxathiepane (782496-42-8) → (2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[N-tert-butoxycarbonyl-1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine (782496-47-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrabutylammonium azide / tetrahydrofuran / 36 h / 35 °C

1.2: H₂SO₄ / tetrahydrofuran / 8 h / pH 1 - 2

1.3: 330 mg / MsCl; Et₃N / CH₂Cl₂ / 1 h / -40 - -15 °C

2.1: 69 percent / tetrahydrofuran; H₂O / 24 h / 60 °C / pH 10

With tetrabutylammoniun azide; In tetrahydrofuran; water;

DOI:10.1002/chem.200400181

upstream raw materials:

(2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine

di-tert-butyl dicarbonate

(2S/R,4R,7R,2'S,5'S,1''S)-4-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-7-[1''-N''-benzyl-(p-tolylsulfonyl)amino]-ethyl-2,2-dioxo-1,3-dioxathiepane