(-)-(Z,S_S,2R,3R)-5-(N-methyl-S-phenylsulfonimidoyl)-2-hydroxy-3-isopropylpent-4-enoic acid ethyl ester

Base Information

• Chemical Name: (-)-(Z,S_S,2R,3R)-5-(N-methyl-S-phenylsulfonimidoyl)-2-hydroxy-3-isopropylpent-4-enoic acid ethyl ester
• CAS No.: 898237-54-2
• Molecular Formula: C₁₇H₂₅NO₄S
• Molecular Weight: 339.456

Synonyms:(-)-(Z,S_S,2R,3R)-5-(N-methyl-S-phenylsulfonimidoyl)-2-hydroxy-3-isopropylpent-4-enoic acid ethyl ester

Chemical Property of (-)-(Z,S_S,2R,3R)-5-(N-methyl-S-phenylsulfonimidoyl)-2-hydroxy-3-isopropylpent-4-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (-)-(Z,S_S,2R,3R)-5-(N-methyl-S-phenylsulfonimidoyl)-2-hydroxy-3-isopropylpent-4-enoic acid ethyl ester

There total 6 articles about (-)-(Z,S_S,2R,3R)-5-(N-methyl-S-phenylsulfonimidoyl)-2-hydroxy-3-isopropylpent-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: 36.0%

glyoxylic acid ethyl ester (924-44-7) + (CH3)2CHCHCHCH2S(O)(C6H5)NCH3 → (-)-(Z,SS,2R,3R)-5-(N-methyl-S-phenylsulfonimidoyl)-2-hydroxy-3-isopropylpent-4-enoic acid ethyl ester (898237-54-2)

Guidance literature:

(CH₃)2CHCHCHCH₂S(O)(C₆H₅)NCH₃; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.75h;

With triisopropoxytitanium(IV) chloride; In tetrahydrofuran; at -78 ℃; for 1.5h;

glyoxylic acid ethyl ester; In tetrahydrofuran; at -78 ℃; for 4h;

DOI:10.1021/ja061152i

Reference yield:

C13H19NOS → (-)-(Z,SS,2R,3R)-5-(N-methyl-S-phenylsulfonimidoyl)-2-hydroxy-3-isopropylpent-4-enoic acid ethyl ester (898237-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diazabicyclo[5.4.0]undec-7-ene / acetonitrile

2.1: n-BuLi / tetrahydrofuran / 0.75 h / -78 °C

2.2: ClTi(OiPr)3 / tetrahydrofuran / 1.5 h / -78 °C

2.3: 36 percent / tetrahydrofuran / 4 h / -78 °C

With n-butyllithium; 1,2-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ja061152i

Reference yield:

C15H23NO4S → (-)-(Z,SS,2R,3R)-5-(N-methyl-S-phenylsulfonimidoyl)-2-hydroxy-3-isopropylpent-4-enoic acid ethyl ester (898237-54-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diazabicylco[5.4.0]undec-7-ene / hexane; tetrahydrofuran / -78 - 20 °C

2.1: diazabicyclo[5.4.0]undec-7-ene / acetonitrile

3.1: n-BuLi / tetrahydrofuran / 0.75 h / -78 °C

3.2: ClTi(OiPr)3 / tetrahydrofuran / 1.5 h / -78 °C

3.3: 36 percent / tetrahydrofuran / 4 h / -78 °C

With n-butyllithium; 1,2-diazabicyclo[5.4.0]undec-7-ene; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1021/ja061152i

upstream raw materials:

glyoxylic acid ethyl ester

N,S-dimethyl-S-phenylsulfoximine

(+)-(Z,S)-4-methyl-1-(N-methyl-S-phenylsulfonimidoyl)-pent-2-ene

isovaleraldehyde

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