(5S,6S)-5-((Z)-but-1-en-3-ynyl)-11,11-dimethyl-10,10-diphenyl-2,4,9-trioxa-10-siladodecan-6-yl 2-((E)-2-iodovinyl)-6-methoxybenzoate

Base Information

Chemical Name:(5S,6S)-5-((Z)-but-1-en-3-ynyl)-11,11-dimethyl-10,10-diphenyl-2,4,9-trioxa-10-siladodecan-6-yl 2-((E)-2-iodovinyl)-6-methoxybenzoate
CAS No.:1333235-35-0
Molecular Formula:C₃₆H₄₁IO₆Si
Molecular Weight:724.708
Hs Code.:

Synonyms:(5S,6S)-5-((Z)-but-1-en-3-ynyl)-11,11-dimethyl-10,10-diphenyl-2,4,9-trioxa-10-siladodecan-6-yl 2-((E)-2-iodovinyl)-6-methoxybenzoate

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Chemical Property of (5S,6S)-5-((Z)-but-1-en-3-ynyl)-11,11-dimethyl-10,10-diphenyl-2,4,9-trioxa-10-siladodecan-6-yl 2-((E)-2-iodovinyl)-6-methoxybenzoate

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Technology Process of (5S,6S)-5-((Z)-but-1-en-3-ynyl)-11,11-dimethyl-10,10-diphenyl-2,4,9-trioxa-10-siladodecan-6-yl 2-((E)-2-iodovinyl)-6-methoxybenzoate

There total 7 articles about (5S,6S)-5-((Z)-but-1-en-3-ynyl)-11,11-dimethyl-10,10-diphenyl-2,4,9-trioxa-10-siladodecan-6-yl 2-((E)-2-iodovinyl)-6-methoxybenzoate 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: 89.0%

: 1240382-69-7
(E)-5-(2-iodovinyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

: 1333235-41-8
(5S,6S)-5-((Z)-but-1-en-3-ynyl)-11,11-dimethyl-10,10-diphenyl-2,4,9-trioxa-10-siladodecan-6-ol

: 77-78-1
dimethyl sulfate

: 1333235-35-0
(5S,6S)-5-((Z)-but-1-en-3-ynyl)-11,11-dimethyl-10,10-diphenyl-2,4,9-trioxa-10-siladodecan-6-yl 2-((E)-2-iodovinyl)-6-methoxybenzoate

Guidance literature:: (5S,6S)-5-((Z)-but-1-en-3-ynyl)-11,11-dimethyl-10,10-diphenyl-2,4,9-trioxa-10-siladodecan-6-ol; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 1h;

(E)-5-(2-iodovinyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one; In tetrahydrofuran; at 0 ℃; for 2h;

dimethyl sulfate; In tetrahydrofuran; at 0 - 20 ℃; for 3h;
DOI:10.1002/anie.201103081

Reference yield:

: 1333235-58-7
(5S,6S)-6-(tert-butyldimethylsilyloxy)-10,10,11,11-tetramethyl-5-vinyl-2,4,9-trioxa-10-siladodecane

: 1333235-35-0
(5S,6S)-5-((Z)-but-1-en-3-ynyl)-11,11-dimethyl-10,10-diphenyl-2,4,9-trioxa-10-siladodecan-6-yl 2-((E)-2-iodovinyl)-6-methoxybenzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: ozone / dichloromethane / -78 °C

1.2: -78 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / -78 - -20 °C

2.2: 2 h / -78 °C

2.3: 22 h / 20 °C

3.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 20 °C

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C

4.2: 2 h / 0 °C

4.3: 3 h / 0 - 20 °C

With 1H-imidazole; dmap; n-butyllithium; sodium hexamethyldisilazane; ozone; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 2.1: Peterson olefination / 2.2: Peterson olefination;
DOI:10.1002/anie.201103081

Reference yield:

: C₁₉H₄₂O₅Si₂

: 1333235-35-0
(5S,6S)-5-((Z)-but-1-en-3-ynyl)-11,11-dimethyl-10,10-diphenyl-2,4,9-trioxa-10-siladodecan-6-yl 2-((E)-2-iodovinyl)-6-methoxybenzoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 - -20 °C

1.2: 2 h / -78 °C

1.3: 22 h / 20 °C

2.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 20 °C

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C

3.2: 2 h / 0 °C

3.3: 3 h / 0 - 20 °C

With 1H-imidazole; dmap; n-butyllithium; sodium hexamethyldisilazane; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1.1: Peterson olefination / 1.2: Peterson olefination;
DOI:10.1002/anie.201103081