(3S,4E,6S)-3,6-dimethyl-7-(p-tolylsulfonyloxy)-3-(tolylsulfonyloxymethyl)hepta-1,4-diene

Base Information

• Chemical Name: (3S,4E,6S)-3,6-dimethyl-7-(p-tolylsulfonyloxy)-3-(tolylsulfonyloxymethyl)hepta-1,4-diene
• CAS No.: 112763-53-8
• Molecular Formula: C₂₄H₃₀O₆S₂
• Molecular Weight: 478.631
• Mol file: 112763-53-8.mol

Synonyms:(3S,4E,6S)-3,6-dimethyl-7-(p-tolylsulfonyloxy)-3-(tolylsulfonyloxymethyl)hepta-1,4-diene

Chemical Property of (3S,4E,6S)-3,6-dimethyl-7-(p-tolylsulfonyloxy)-3-(tolylsulfonyloxymethyl)hepta-1,4-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4E,6S)-3,6-dimethyl-7-(p-tolylsulfonyloxy)-3-(tolylsulfonyloxymethyl)hepta-1,4-diene

There total 28 articles about (3S,4E,6S)-3,6-dimethyl-7-(p-tolylsulfonyloxy)-3-(tolylsulfonyloxymethyl)hepta-1,4-diene 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: 74.0%

(E)-(2S,5S)-2,5-Dimethyl-2-vinyl-hex-3-ene-1,6-diol (112763-52-7) + p-toluenesulfonyl chloride (98-59-9) → (3S,4E,6S)-3,6-dimethyl-7-(p-tolylsulfonyloxy)-3-(tolylsulfonyloxymethyl)hepta-1,4-diene (112763-53-8)

Guidance literature:

With pyridine; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1021/ja00213a047

Reference yield:

(3S)-4-(methoxymethoxy)-3-methylbutyronitrile (112763-38-9) → (3S,4E,6S)-3,6-dimethyl-7-(p-tolylsulfonyloxy)-3-(tolylsulfonyloxymethyl)hepta-1,4-diene (112763-53-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / (i-Bu)2AlH / diethyl ether / 4 h / Ambient temperature

2: 77 percent / toluene / 6 h / Heating

3: 1) KOH, MeOH 2) (i-Pr)2NEt / 1) reflux, 2 h. 2) CH₂Cl₂ room temperature, 4 h.

4: (i-Pr)2NLi-HMPA / tetrahydrofuran / 4 h / Ambient temperature

5: 98 percent / (i-Pr)2NEt / CH₂Cl₂ / 4 h / Ambient temperature

6: 98 percent / LiAlH₄ / diethyl ether / 4 h / Ambient temperature

7: 60 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

8: 70 percent / tetrahydrofuran / 1 h / Ambient temperature

9: 99 percent / HCl / methanol / 1 h / Heating

10: 74 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

With pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; hydrogenchloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1021/ja00213a047

Reference yield:

(3S)-4-(methoxymethoxy)-3-methylbutanal (112763-39-0) → (3S,4E,6S)-3,6-dimethyl-7-(p-tolylsulfonyloxy)-3-(tolylsulfonyloxymethyl)hepta-1,4-diene (112763-53-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 77 percent / toluene / 6 h / Heating

2: 1) KOH, MeOH 2) (i-Pr)2NEt / 1) reflux, 2 h. 2) CH₂Cl₂ room temperature, 4 h.

3: (i-Pr)2NLi-HMPA / tetrahydrofuran / 4 h / Ambient temperature

4: 98 percent / (i-Pr)2NEt / CH₂Cl₂ / 4 h / Ambient temperature

5: 98 percent / LiAlH₄ / diethyl ether / 4 h / Ambient temperature

6: 60 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

7: 70 percent / tetrahydrofuran / 1 h / Ambient temperature

8: 99 percent / HCl / methanol / 1 h / Heating

9: 74 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

With pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; hydrogenchloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1021/ja00213a047

upstream raw materials:

(E)-(2S,5S)-2,5-Dimethyl-2-vinyl-hex-3-ene-1,6-diol

p-toluenesulfonyl chloride

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol

((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol