(2R,6R)-2-[(E)-(S)-1,3-Dimethyl-4-(toluene-4-sulfonyl)-but-1-enyl]-6-ethyl-5-methyl-3,6-dihydro-2H-pyran

Base Information

• Chemical Name: (2R,6R)-2-[(E)-(S)-1,3-Dimethyl-4-(toluene-4-sulfonyl)-but-1-enyl]-6-ethyl-5-methyl-3,6-dihydro-2H-pyran
• CAS No.: 130799-16-5
• Molecular Formula: C₂₁H₃₀O₃S
• Molecular Weight: 362.533
• Mol file: 130799-16-5.mol

Synonyms:(2R,6R)-2-[(E)-(S)-1,3-Dimethyl-4-(toluene-4-sulfonyl)-but-1-enyl]-6-ethyl-5-methyl-3,6-dihydro-2H-pyran

Chemical Property of (2R,6R)-2-[(E)-(S)-1,3-Dimethyl-4-(toluene-4-sulfonyl)-but-1-enyl]-6-ethyl-5-methyl-3,6-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6R)-2-[(E)-(S)-1,3-Dimethyl-4-(toluene-4-sulfonyl)-but-1-enyl]-6-ethyl-5-methyl-3,6-dihydro-2H-pyran

There total 12 articles about (2R,6R)-2-[(E)-(S)-1,3-Dimethyl-4-(toluene-4-sulfonyl)-but-1-enyl]-6-ethyl-5-methyl-3,6-dihydro-2H-pyran 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: 71.0%

(E)-(S)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-2-(toluene-4-sulfonyl)-hex-4-enoic acid methyl ester (130799-15-4) → (2R,6R)-2-[(E)-(S)-1,3-Dimethyl-4-(toluene-4-sulfonyl)-but-1-enyl]-6-ethyl-5-methyl-3,6-dihydro-2H-pyran (130799-16-5)

Guidance literature:

With tetramethyl ammonium acetate; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 100 ℃; for 17h;

Reference yield:

p-toluenesulfonyl fluoride (455-16-3) → (2R,6R)-2-[(E)-(S)-1,3-Dimethyl-4-(toluene-4-sulfonyl)-but-1-enyl]-6-ethyl-5-methyl-3,6-dihydro-2H-pyran (130799-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, -78 deg C, 2.) -78 deg C to RT, 24 h

2: 71 percent / Me₄NOAc / hexamethylphosphoric acid triamide / 17 h / 100 °C

With tetramethyl ammonium acetate; lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide;

Reference yield:

(E)-3-methyl-1,3-hexadiene (105247-06-1) → (2R,6R)-2-[(E)-(S)-1,3-Dimethyl-4-(toluene-4-sulfonyl)-but-1-enyl]-6-ethyl-5-methyl-3,6-dihydro-2H-pyran (130799-16-5)

Guidance literature:

Multi-step reaction with 8 steps

1: hydroquinone / CHCl₃ / 12 h / 120 °C

3: 1.) (COCl)2, DMF, 2.) PhCH₂PdCl(PPh₃)2 / 1.) CH₂Cl₂, 0 deg C - 20 deg C, 2 h, 2.) HMPA, 70 deg C, 3 h

4: 92 percent / tetrahydrofuran / 2 h / 0 °C

6: 92 percent / diethyl ether / Ambient temperature

7: 1.) LDA / 1.) THF, -78 deg C, 2.) -78 deg C to RT, 24 h

8: 71 percent / Me₄NOAc / hexamethylphosphoric acid triamide / 17 h / 100 °C

With oxalyl dichloride; trans benzyl(chloro)bis(triphenylphosphine)palladium(II); tetramethyl ammonium acetate; N,N-dimethyl-formamide; hydroquinone; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; chloroform;

upstream raw materials:

(E)-(S)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-2-(toluene-4-sulfonyl)-hex-4-enoic acid methyl ester

p-toluenesulfonyl fluoride

(E)-3-methyl-1,3-hexadiene

(E)-1-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-but-2-en-1-one

Downstream raw materials:

methyl 5β,6α-dibenzyloxypolyangioate

5β,6α-dibenzyloxypolyangioic acid

(+)-ambruticin S