(1E,4S,5R,6R,7S)-5,7-dimethyl-1-iodo-4-[(2E)-3-phenylacryloxy]-oct-1-en-6-ol

Base Information

Chemical Name:(1E,4S,5R,6R,7S)-5,7-dimethyl-1-iodo-4-[(2E)-3-phenylacryloxy]-oct-1-en-6-ol
CAS No.:781642-45-3
Molecular Formula:C₂₀H₂₇IO₃
Molecular Weight:442.337
Hs Code.:

Synonyms:(1E,4S,5R,6R,7S)-5,7-dimethyl-1-iodo-4-[(2E)-3-phenylacryloxy]-oct-1-en-6-ol

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Chemical Property of (1E,4S,5R,6R,7S)-5,7-dimethyl-1-iodo-4-[(2E)-3-phenylacryloxy]-oct-1-en-6-ol

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Technology Process of (1E,4S,5R,6R,7S)-5,7-dimethyl-1-iodo-4-[(2E)-3-phenylacryloxy]-oct-1-en-6-ol

There total 8 articles about (1E,4S,5R,6R,7S)-5,7-dimethyl-1-iodo-4-[(2E)-3-phenylacryloxy]-oct-1-en-6-ol 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: 69.0%

: 781642-44-2
(1E,4S,5R,6R,7S)-1-iodo-5,7-dimethyl-4-[(2E)-3-phenylacryloxy]-6-methoxymethoxy-oct-1-ene

: 781642-45-3
(1E,4S,5R,6R,7S)-5,7-dimethyl-1-iodo-4-[(2E)-3-phenylacryloxy]-oct-1-en-6-ol

Guidance literature:: With boron trichloride; In hexane; dichloromethane; at -78 ℃; for 4h;
DOI:10.1021/ol048574m

Reference yield:

: 781642-33-9
(3S,4R,5R,6S)-8-(benzyloxy)-3,5-dimethyl-6-(triisopropylsilyloxy)-oct-1-en-4-ol

: 781642-45-3
(1E,4S,5R,6R,7S)-5,7-dimethyl-1-iodo-4-[(2E)-3-phenylacryloxy]-oct-1-en-6-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 84 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 18 h / 0 - 20 °C

2: 86 percent / H₂ / Pd/C / methanol / 24 h

3: 98 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4: CrCl₂ / dioxane; tetrahydrofuran / 20 h / 0 - 20 °C

5: 96 percent / HF; pyridine / tetrahydrofuran / 68 h

6: 85 percent / Et₃N; DMAP / CH₂Cl₂ / 96 h

7: 69 percent / BCl₃ / CH₂Cl₂; hexane / 4 h / -78 °C

With pyridine; chromium dichloride; dmap; oxalyl dichloride; hydrogen fluoride; hydrogen; boron trichloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; 3: Swern oxidation / 4: Takai's iodoolefination;
DOI:10.1021/ol048574m

Reference yield:

: 781642-37-3
(3S,4R,5R,6S)-8-(benzyloxy)-3,5-dimethyl-4-methoxymethoxy-6-(triisopropylsilyloxy)-oct-1-ene

: 781642-45-3
(1E,4S,5R,6R,7S)-5,7-dimethyl-1-iodo-4-[(2E)-3-phenylacryloxy]-oct-1-en-6-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / H₂ / Pd/C / methanol / 24 h

2: 98 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3: CrCl₂ / dioxane; tetrahydrofuran / 20 h / 0 - 20 °C

4: 96 percent / HF; pyridine / tetrahydrofuran / 68 h

5: 85 percent / Et₃N; DMAP / CH₂Cl₂ / 96 h

6: 69 percent / BCl₃ / CH₂Cl₂; hexane / 4 h / -78 °C

With pyridine; chromium dichloride; dmap; oxalyl dichloride; hydrogen fluoride; hydrogen; boron trichloride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; 2: Swern oxidation / 3: Takai's iodoolefination;
DOI:10.1021/ol048574m