(2R,3S,4S,5S,6S,7Z)-1-iodo-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-diene

Base Information

Chemical Name:(2R,3S,4S,5S,6S,7Z)-1-iodo-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-diene
CAS No.:216669-69-1
Molecular Formula:C₂₇H₄₅IO₃Si
Molecular Weight:572.643
Hs Code.:

Synonyms:(2R,3S,4S,5S,6S,7Z)-1-iodo-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-diene

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Chemical Property of (2R,3S,4S,5S,6S,7Z)-1-iodo-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-diene

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Technology Process of (2R,3S,4S,5S,6S,7Z)-1-iodo-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-diene

There total 13 articles about (2R,3S,4S,5S,6S,7Z)-1-iodo-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-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: 95.0%

: 216669-64-6
(2S,3R,4R,5S,6S,7Z)-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dien-1-ol

: 216669-69-1
(2R,3S,4S,5S,6S,7Z)-1-iodo-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-diene

Guidance literature:: With iodine; triphenylphosphine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ja043168j

Reference yield:

: 851889-70-8
(3E,5S,6S,7R,8R,9S)-6-hydroxy-8,10-[(R)-4-methoxybenzilidenedioxy]-5,7,9-trimethyldec-3-enoic acid methyl ester

: 216669-69-1
(2R,3S,4S,5S,6S,7Z)-1-iodo-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-diene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

2.1: ozone; pyridine / methanol / -78 °C

2.2: dimethyl sulfide / methanol / -78 - 0 °C

3.1: diethyl ether / 48 h / 20 °C

4.1: 5.6 g / NaH / tetrahydrofuran / 3 h / 20 °C

5.1: 83 percent / diisobutylaluminium hydride / CH₂Cl₂; hexane / -78 - -50 °C

6.1: 95 percent / triphenylphosphine; I₂ / CH₂Cl₂ / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; iodine; sodium hydride; diisobutylaluminium hydride; ozone; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; 4.1: Peterson elimination;
DOI:10.1021/ja043168j

Reference yield:

: 216670-83-6
(2R,3R,4S)-4-[(2R,4R,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methyl-3-triethylsilanyloxy-pentanal

: 216669-69-1
(2R,3S,4S,5S,6S,7Z)-1-iodo-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-diene

Guidance literature:: Multi-step reaction with 4 steps

1: diethyl ether / 48 h / 20 °C

2: 5.6 g / NaH / tetrahydrofuran / 3 h / 20 °C

3: 83 percent / diisobutylaluminium hydride / CH₂Cl₂; hexane / -78 - -50 °C

4: 95 percent / triphenylphosphine; I₂ / CH₂Cl₂ / 0 - 20 °C

With iodine; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 2: Peterson elimination;
DOI:10.1021/ja043168j