[(2R)-2-[(1S,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-pent-4-enyloxymethyl]-benzene

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Chemical Name:[(2R)-2-[(1S,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-pent-4-enyloxymethyl]-benzene
CAS No.:284471-68-7
Molecular Formula:C₃₀H₅₄O₄Si₂
Molecular Weight:534.927
Hs Code.:

Synonyms:[(2R)-2-[(1S,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-pent-4-enyloxymethyl]-benzene

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Chemical Property of [(2R)-2-[(1S,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-pent-4-enyloxymethyl]-benzene

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Technology Process of [(2R)-2-[(1S,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-pent-4-enyloxymethyl]-benzene

There total 9 articles about [(2R)-2-[(1S,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-pent-4-enyloxymethyl]-benzene 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: 91.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 284471-83-6
(2S,3S)-2-((R)-1-Benzyloxymethyl-but-3-enyloxy)-hex-5-ene-1,3-diol

: 284471-68-7
[(2R)-2-[(1S,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-pent-4-enyloxymethyl]-benzene

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 25 ℃; for 1h;
DOI:10.1021/ja0007197

Reference yield:

: 58931-16-1,88981-35-5,110339-28-1
(R)-1-benzyloxypent-4-en-2-ol

: 284471-68-7
[(2R)-2-[(1S,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-pent-4-enyloxymethyl]-benzene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 93 percent / NaH / tetrahydrofuran / 14 h / 25 °C

2.1: oxalyl chloride / DMF / CH₂Cl₂ / 2 h / 25 °C

3.1: 1.98 g / Et₃N / CH₂Cl₂ / 0 - 25 °C

4.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 2.5 h / -78 °C

4.2: 57 percent / CH₂Cl₂ / 1 h / -78 °C

5.1: 80 percent / LiBH₄ / methanol; diethyl ether; tetrahydrofuran / 2 h / 0 °C

6.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 25 °C

With 2,6-dimethylpyridine; lithium borohydride; oxalyl dichloride; titanium tetrachloride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.1: Alkylation / 2.1: Substitution / 3.1: Acylation / 4.1: complexation / 4.2: aldol reaction / 5.1: reductive deprotection / 6.1: silylation;
DOI:10.1021/ja0007197

Reference yield:

: 239075-68-4
(R)-1-(benzyloxymethyl)but-3-enyl-1-oxyacetic acid

: 284471-68-7
[(2R)-2-[(1S,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-pent-4-enyloxymethyl]-benzene

Guidance literature:: Multi-step reaction with 5 steps

1.1: oxalyl chloride / DMF / CH₂Cl₂ / 2 h / 25 °C

2.1: 1.98 g / Et₃N / CH₂Cl₂ / 0 - 25 °C

3.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 2.5 h / -78 °C

3.2: 57 percent / CH₂Cl₂ / 1 h / -78 °C

4.1: 80 percent / LiBH₄ / methanol; diethyl ether; tetrahydrofuran / 2 h / 0 °C

5.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 25 °C

With 2,6-dimethylpyridine; lithium borohydride; oxalyl dichloride; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.1: Substitution / 2.1: Acylation / 3.1: complexation / 3.2: aldol reaction / 4.1: reductive deprotection / 5.1: silylation;
DOI:10.1021/ja0007197