(+)-(E,S_S,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-cyclohexyl-2-[(2-methylprop-2-yl-sulfonyl)-prop-2-ynyl-amino]pent-4-enoic acid ethyl ester

Base Information

• Chemical Name: (+)-(E,S_S,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-cyclohexyl-2-[(2-methylprop-2-yl-sulfonyl)-prop-2-ynyl-amino]pent-4-enoic acid ethyl ester
• CAS No.: 616234-12-9
• Molecular Formula: C₂₇H₄₀N₂O₅S₂
• Molecular Weight: 536.757

Synonyms:(+)-(E,S_S,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-cyclohexyl-2-[(2-methylprop-2-yl-sulfonyl)-prop-2-ynyl-amino]pent-4-enoic acid ethyl ester

Chemical Property of (+)-(E,S_S,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-cyclohexyl-2-[(2-methylprop-2-yl-sulfonyl)-prop-2-ynyl-amino]pent-4-enoic acid ethyl ester

Chemical Property:

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Technology Process of (+)-(E,S_S,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-cyclohexyl-2-[(2-methylprop-2-yl-sulfonyl)-prop-2-ynyl-amino]pent-4-enoic acid ethyl ester

There total 3 articles about (+)-(E,S_S,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-cyclohexyl-2-[(2-methylprop-2-yl-sulfonyl)-prop-2-ynyl-amino]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: 91.0%

propargyl bromide (106-96-7) + C6H11C18H27O5N2S2 (445010-35-5) → (+)-(E,SS,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-cyclohexyl-2-[(2-methylprop-2-yl-sulfonyl)-prop-2-ynyl-amino]pent-4-enoic acid ethyl ester (616234-12-9)

Guidance literature:

C₆H₁₁C₁₈H₂₇O₅N₂S₂; With CsCO₃; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h;

propargyl bromide; In N,N-dimethyl-formamide; toluene; at 0 - 20 ℃;

DOI:10.1021/jo030171x

Reference yield:

(+)-(E,S)-3-cyclohexyl-1-(N-methyl-S-phenylsulfonimidoyl)-prop-2-ene (329770-66-3) → (+)-(E,SS,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-cyclohexyl-2-[(2-methylprop-2-yl-sulfonyl)-prop-2-ynyl-amino]pent-4-enoic acid ethyl ester (616234-12-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran / -78 °C

1.2: ClTi(Oi-Pr)3 / tetrahydrofuran / -78 °C

1.3: 77 percent / tetrahydrofuran / -78 °C

2.1: CsCO₃ / dimethylformamide / 0.25 h / 20 °C

2.2: 91 percent / dimethylformamide; toluene / 0 - 20 °C

With n-butyllithium; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo030171x

Reference yield:

(2-methyl-propane-2-sulfonylimino) acetic acid ethyl ester (445010-18-4) → (+)-(E,SS,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-cyclohexyl-2-[(2-methylprop-2-yl-sulfonyl)-prop-2-ynyl-amino]pent-4-enoic acid ethyl ester (616234-12-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran / -78 °C

1.2: ClTi(Oi-Pr)3 / tetrahydrofuran / -78 °C

1.3: 77 percent / tetrahydrofuran / -78 °C

2.1: CsCO₃ / dimethylformamide / 0.25 h / 20 °C

2.2: 91 percent / dimethylformamide; toluene / 0 - 20 °C

With n-butyllithium; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo030171x

upstream raw materials:

propargyl bromide

C₆H₁₁C₁₈H₂₇O₅N₂S₂

(+)-(E,S)-3-cyclohexyl-1-(N-methyl-S-phenylsulfonimidoyl)-prop-2-ene

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

Downstream raw materials:

Benzenesulfinic acid (R)-methylamide

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