(+)-(E,S_S,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-methyl-2-[(2-methylprop-2-ylsulfonyl)-prop-2-ynylamino]-pent-4-enoic acid ethyl ester

Base Information

• Chemical Name: (+)-(E,S_S,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-methyl-2-[(2-methylprop-2-ylsulfonyl)-prop-2-ynylamino]-pent-4-enoic acid ethyl ester
• CAS No.: 616234-10-7
• Molecular Formula: C₂₂H₃₂N₂O₅S₂
• Molecular Weight: 468.638
• Mol file: 616234-10-7.mol

Synonyms:(+)-(E,S_S,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-methyl-2-[(2-methylprop-2-ylsulfonyl)-prop-2-ynylamino]-pent-4-enoic acid ethyl ester

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (+)-(E,S_S,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-methyl-2-[(2-methylprop-2-ylsulfonyl)-prop-2-ynylamino]-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: 95.0%

propargyl bromide (106-96-7) + C19H30N2O5S2 → (+)-(E,SS,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-methyl-2-[(2-methylprop-2-ylsulfonyl)-prop-2-ynylamino]-pent-4-enoic acid ethyl ester (616234-10-7)

Guidance literature:

C₁₉H₃₀N₂O₅S₂; 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:

(2-methyl-propane-2-sulfonylimino) acetic acid ethyl ester (445010-18-4) → (+)-(E,SS,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-methyl-2-[(2-methylprop-2-ylsulfonyl)-prop-2-ynylamino]-pent-4-enoic acid ethyl ester (616234-10-7)

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: 67 percent / tetrahydrofuran / -78 °C

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

2.2: 95 percent / dimethylformamide; toluene / 0 - 20 °C

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

DOI:10.1021/jo030171x

Reference yield: 49.0%

(+)-(E,SS,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-methyl-2-[(2-methylprop-2-ylsulfonyl)-prop-2-ynylamino]-pent-4-enoic acid ethyl ester (616234-10-7) → Benzenesulfinic acid (R)-methylamide (33957-73-2,69726-27-8,84413-63-8,33993-55-4) + (-)-(3S,4R,4aR)-2,3,4,4a,5,6-hexahydro-4-methyl-2-(2-methylprop-2-yl-sulfonyl)-6-oxo-1H-cyclopenta[c]pyridine-3-carboxylic acid ethyl ester

Guidance literature:

(+)-(E,S_S,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-methyl-2-[(2-methylprop-2-ylsulfonyl)-prop-2-ynylamino]-pent-4-enoic acid ethyl ester; Co₂(CO)8; In tetrahydrofuran; for 0.5h;

With N-methyl-2-indolinone; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/jo030171x

upstream raw materials:

propargyl bromide

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

Downstream raw materials:

Benzenesulfinic acid (R)-methylamide