4-Decenoic acid, 3-[(2S)-3-iodo-2-(methoxymethoxy)propyl]-9-(phenylmethoxy)-, ethyl ester, (3R,4E,9S)-

Base Information

Chemical Name:4-Decenoic acid, 3-[(2S)-3-iodo-2-(methoxymethoxy)propyl]-9-(phenylmethoxy)-, ethyl ester, (3R,4E,9S)-
CAS No.:403694-62-2
Molecular Formula:C24H37IO5
Molecular Weight:532.459
Hs Code.:

Synonyms:

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Chemical Property of 4-Decenoic acid, 3-[(2S)-3-iodo-2-(methoxymethoxy)propyl]-9-(phenylmethoxy)-, ethyl ester, (3R,4E,9S)-

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Technology Process of 4-Decenoic acid, 3-[(2S)-3-iodo-2-(methoxymethoxy)propyl]-9-(phenylmethoxy)-, ethyl ester, (3R,4E,9S)-

There total 8 articles about 4-Decenoic acid, 3-[(2S)-3-iodo-2-(methoxymethoxy)propyl]-9-(phenylmethoxy)-, ethyl ester, (3R,4E,9S)- 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: 85.0%

: 165817-42-5
(3R,4E,9S)-9-benzyloxy-3-[(2S)-3-hydroxy-2-methoxymethoxypropyl]dec-4-enoic acid ethyl ester

: 403694-62-2
(3R,4E,9S)-9-benzyloxy-3-[(2S)-3-iodo-2-methoxymethoxypropyl]dec-4-enoic acid ethyl ester

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In diethyl ether; acetonitrile; at 20 ℃; for 0.5h;
DOI:10.1021/jo010743i

Reference yield:

: 165817-36-7
(2R,4E,6S)-6-benzyloxy-2-(4-methoxybenzyloxy)hept-4-enoic acid methyl ester

: 403694-62-2
(3R,4E,9S)-9-benzyloxy-3-[(2S)-3-iodo-2-methoxymethoxypropyl]dec-4-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 82 percent / H₂; n-BuNH₂ / Pd/C / ethyl acetate / 3 h / 20 °C / 1551.49 Torr

2.1: DIBALH / diethyl ether / 1 h / -78 °C

2.2: 63 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C

3.1: 93 percent / DMAP; DCC / CH₂Cl₂ / 3 h / 20 °C

4.1: LHMDS; TMSCl; Et₃N / tetrahydrofuran / -78 - 20 °C

4.2: 86 percent / diethyl ether / 0.5 h / 20 °C

5.1: 86 percent / DDQ / CH₂Cl₂; H₂O / 0.33 h / 20 °C

6.1: 84 percent / PhOH / 4.5 h / 125 °C

7.1: 97 percent / NaBH₄ / ethanol / 8 h / 20 °C

8.1: 85 percent / I₂; Ph₃P; imidazole / diethyl ether; acetonitrile / 0.5 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; chloro-trimethyl-silane; hydrogen; iodine; diisobutylaluminium hydride; N-butylamine; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; phenol; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; acetonitrile; 4.1: Ireland-Claisen rearrangement / 6.1: Claisen rearrangement;
DOI:10.1021/jo010743i

Reference yield:

: 165817-40-3
(2S,4E,6R,10S)-10-benzyloxy-6-hydroxy-2-methoxymethoxyundec-4-enoic acid methyl ester

: 403694-62-2
(3R,4E,9S)-9-benzyloxy-3-[(2S)-3-iodo-2-methoxymethoxypropyl]dec-4-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / PhOH / 4.5 h / 125 °C

2: 97 percent / NaBH₄ / ethanol / 8 h / 20 °C

3: 85 percent / I₂; Ph₃P; imidazole / diethyl ether; acetonitrile / 0.5 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; iodine; triphenylphosphine; phenol; In diethyl ether; ethanol; acetonitrile; 1: Claisen rearrangement;
DOI:10.1021/jo010743i