(E)-(2S,3R)-3-Hydroxy-1-[(3S,4S)-5-((E)-(2S,3R)-3-hydroxy-2-methyl-hex-4-enoyl)-1,1-dioxo-3,4-diphenyl-1λ⁶-[1,2,5]thiadiazolidin-2-yl]-2-methyl-hex-4-en-1-one

Base Information

• Chemical Name: (E)-(2S,3R)-3-Hydroxy-1-[(3S,4S)-5-((E)-(2S,3R)-3-hydroxy-2-methyl-hex-4-enoyl)-1,1-dioxo-3,4-diphenyl-1λ⁶-[1,2,5]thiadiazolidin-2-yl]-2-methyl-hex-4-en-1-one
• CAS No.: 145163-09-3
• Molecular Formula: C₂₈H₃₄N₂O₆S
• Molecular Weight: 526.654

Synonyms:

Chemical Property of (E)-(2S,3R)-3-Hydroxy-1-[(3S,4S)-5-((E)-(2S,3R)-3-hydroxy-2-methyl-hex-4-enoyl)-1,1-dioxo-3,4-diphenyl-1λ⁶-[1,2,5]thiadiazolidin-2-yl]-2-methyl-hex-4-en-1-one

Chemical Property:

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Safty Information:

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MSDS Files:

Useful:

Technology Process of (E)-(2S,3R)-3-Hydroxy-1-[(3S,4S)-5-((E)-(2S,3R)-3-hydroxy-2-methyl-hex-4-enoyl)-1,1-dioxo-3,4-diphenyl-1λ⁶-[1,2,5]thiadiazolidin-2-yl]-2-methyl-hex-4-en-1-one

There total 3 articles about (E)-(2S,3R)-3-Hydroxy-1-[(3S,4S)-5-((E)-(2S,3R)-3-hydroxy-2-methyl-hex-4-enoyl)-1,1-dioxo-3,4-diphenyl-1λ⁶-[1,2,5]thiadiazolidin-2-yl]-2-methyl-hex-4-en-1-one 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:

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → (E)-(2S,3R)-3-Hydroxy-1-[(3S,4S)-5-((E)-(2S,3R)-3-hydroxy-2-methyl-hex-4-enoyl)-1,1-dioxo-3,4-diphenyl-1λ6-[1,2,5]thiadiazolidin-2-yl]-2-methyl-hex-4-en-1-one (145163-09-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / H₂NSO₂NH₂ / dimethylsulfoxide / 18 h / 130 °C

2: 95 percent / Et₃N / tetrahydrofuran; CH₂Cl₂ / 0.08 h / 0 °C

3: 1) TiCl₄, diisopropylethylamine / 1) CH₂Cl₂, -78 deg C, 2) -78 deg C, 5 min

With titanium tetrachloride; SULFAMIDE; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)61012-2

Reference yield:

(3S,4S)-3,4-diphenyl-1,2,5-thiadiazolidine 1,1-dioxide (145211-96-7) → (E)-(2S,3R)-3-Hydroxy-1-[(3S,4S)-5-((E)-(2S,3R)-3-hydroxy-2-methyl-hex-4-enoyl)-1,1-dioxo-3,4-diphenyl-1λ6-[1,2,5]thiadiazolidin-2-yl]-2-methyl-hex-4-en-1-one (145163-09-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Et₃N / tetrahydrofuran; CH₂Cl₂ / 0.08 h / 0 °C

2: 1) TiCl₄, diisopropylethylamine / 1) CH₂Cl₂, -78 deg C, 2) -78 deg C, 5 min

With titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)61012-2

Reference yield:

trans-Crotonaldehyde (123-73-9,4170-30-3) + (3S,4S)-2,5-dipropionyl-3,4-diphenyl-1,2,5-thiadiazolidine 1,1-dioxide (145163-05-9) → (E)-(2S,3R)-3-Hydroxy-1-[(3S,4S)-5-((E)-(2S,3R)-3-hydroxy-2-methyl-hex-4-enoyl)-1,1-dioxo-3,4-diphenyl-1λ6-[1,2,5]thiadiazolidin-2-yl]-2-methyl-hex-4-en-1-one (145163-09-3)

Guidance literature:

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; Yield given. Multistep reaction; 1) CH₂Cl₂, -78 deg C, 2) -78 deg C, 5 min;

DOI:10.1016/S0040-4039(00)61012-2

upstream raw materials:

trans-Crotonaldehyde

(3S,4S)-2,5-dipropionyl-3,4-diphenyl-1,2,5-thiadiazolidine 1,1-dioxide

(S,S)-1,2-diphenyl-1,2-diaminoethane

(3S,4S)-3,4-diphenyl-1,2,5-thiadiazolidine 1,1-dioxide

Downstream raw materials:

(2S,3R)-methyl 2-methyl-3-hydroxy-(E)-4-hexenoate

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