(Z,S_S,2S,3R)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-5-(N-methyl-S-phenylsulfonimidoyl)-2-(tert-butylsulfonylamino)pent-4-enoic acid ethyl ester

Base Information

• Chemical Name: (Z,S_S,2S,3R)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-5-(N-methyl-S-phenylsulfonimidoyl)-2-(tert-butylsulfonylamino)pent-4-enoic acid ethyl ester
• CAS No.: 898237-60-0
• Molecular Formula: C₂₇H₄₈N₂O₆S₂Si
• Molecular Weight: 588.905

Synonyms:(Z,S_S,2S,3R)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-5-(N-methyl-S-phenylsulfonimidoyl)-2-(tert-butylsulfonylamino)pent-4-enoic acid ethyl ester

Chemical Property of (Z,S_S,2S,3R)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-5-(N-methyl-S-phenylsulfonimidoyl)-2-(tert-butylsulfonylamino)pent-4-enoic acid ethyl ester

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Technology Process of (Z,S_S,2S,3R)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-5-(N-methyl-S-phenylsulfonimidoyl)-2-(tert-butylsulfonylamino)pent-4-enoic acid ethyl ester

There total 5 articles about (Z,S_S,2S,3R)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-5-(N-methyl-S-phenylsulfonimidoyl)-2-(tert-butylsulfonylamino)pent-4-enoic acid ethyl 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: 14.0%

(+)-[(S,E)-4-methyl-5-(N-methyl-S-phenylsulfonimidoyl)pent-3-enyloxy]-tert-butyldimethylsilane + (2-methyl-propane-2-sulfonylimino) acetic acid ethyl ester (445010-18-4) → (Z,SS,2S,3R)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-5-(N-methyl-S-phenylsulfonimidoyl)-2-(tert-butylsulfonylamino)pent-4-enoic acid ethyl ester (898237-60-0) + (E,SS,2S,3R)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-5-(N-methyl-S-phenylsulfonimidoyl)-2-(tert-butylsulfonylamino)pent-4-enoic acid ethyl ester

Guidance literature:

(+)-[(S,E)-4-methyl-5-(N-methyl-S-phenylsulfonimidoyl)pent-3-enyloxy]-tert-butyldimethylsilane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With triisopropoxytitanium(IV) chloride; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

(2-methyl-propane-2-sulfonylimino) acetic acid ethyl ester; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 19h;

DOI:10.1021/ja061152i

Reference yield:

C19H33NO2SSi → (Z,SS,2S,3R)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-5-(N-methyl-S-phenylsulfonimidoyl)-2-(tert-butylsulfonylamino)pent-4-enoic acid ethyl ester (898237-60-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaOMe / tetrahydrofuran / 72 h / 20 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.2: ClTi(OiPr)3 / hexane; tetrahydrofuran / 1 h / -78 °C

2.3: 36 percent / hexane; tetrahydrofuran / 19 h / -78 - 20 °C

With n-butyllithium; sodium methylate; In tetrahydrofuran; hexane;

DOI:10.1021/ja061152i

Reference yield:

C22H43NO3SSi2 → (Z,SS,2S,3R)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-5-(N-methyl-S-phenylsulfonimidoyl)-2-(tert-butylsulfonylamino)pent-4-enoic acid ethyl ester (898237-60-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 19 h / -78 - 20 °C

2.1: NaOMe / tetrahydrofuran / 72 h / 20 °C

3.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

3.2: ClTi(OiPr)3 / hexane; tetrahydrofuran / 1 h / -78 °C

3.3: 36 percent / hexane; tetrahydrofuran / 19 h / -78 - 20 °C

With n-butyllithium; sodium methylate; In tetrahydrofuran; hexane;

DOI:10.1021/ja061152i

upstream raw materials:

(2-methyl-propane-2-sulfonylimino) acetic acid ethyl ester

N,S-dimethyl-S-phenylsulfoximine

5-((tert-butyldimethylsilyl)oxy)pentan-2-one

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