[(1S,2R,3R,4R)-3-benzyloxymethoxy-1-(4-methoxybenzyloxymethyl)-2,4-dimethylhex-5-enyloxy]-tert-butyldimethylsilane

Base Information

Chemical Name:[(1S,2R,3R,4R)-3-benzyloxymethoxy-1-(4-methoxybenzyloxymethyl)-2,4-dimethylhex-5-enyloxy]-tert-butyldimethylsilane
CAS No.:475233-01-3
Molecular Formula:C₃₁H₄₈O₅Si
Molecular Weight:528.805
Hs Code.:

Synonyms:[(1S,2R,3R,4R)-3-benzyloxymethoxy-1-(4-methoxybenzyloxymethyl)-2,4-dimethylhex-5-enyloxy]-tert-butyldimethylsilane

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Chemical Property of [(1S,2R,3R,4R)-3-benzyloxymethoxy-1-(4-methoxybenzyloxymethyl)-2,4-dimethylhex-5-enyloxy]-tert-butyldimethylsilane

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Technology Process of [(1S,2R,3R,4R)-3-benzyloxymethoxy-1-(4-methoxybenzyloxymethyl)-2,4-dimethylhex-5-enyloxy]-tert-butyldimethylsilane

There total 6 articles about [(1S,2R,3R,4R)-3-benzyloxymethoxy-1-(4-methoxybenzyloxymethyl)-2,4-dimethylhex-5-enyloxy]-tert-butyldimethylsilane 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:

: 1779-49-3
Methyltriphenylphosphonium bromide

: (2S,3S,4R,5S)-3-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hexanal

: 475233-01-3
[(1S,2R,3R,4R)-3-benzyloxymethoxy-1-(4-methoxybenzyloxymethyl)-2,4-dimethylhex-5-enyloxy]-tert-butyldimethylsilane

Guidance literature:: Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; at 0 ℃; for 4h;

(2S,3S,4R,5S)-3-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hexanal; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.416667h;
DOI:10.1016/S0040-4020(02)00723-8

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 475233-01-3
[(1S,2R,3R,4R)-3-benzyloxymethoxy-1-(4-methoxybenzyloxymethyl)-2,4-dimethylhex-5-enyloxy]-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 74 percent / i-Pr₂NEt / CH₂Cl₂ / 192 h / 20 °C

2.1: DIBAL-H / tetrahydrofuran / 0.5 h / -78 °C

3.1: NaHMDS / tetrahydrofuran; diethyl ether / 4 h / 0 °C

3.2: 0.106 g / diethyl ether; tetrahydrofuran / 0.42 h / 0 °C

With sodium hexamethyldisilazane; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 3.2: Wittig reaction;
DOI:10.1016/S0040-4020(02)00723-8

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 475233-01-3
[(1S,2R,3R,4R)-3-benzyloxymethoxy-1-(4-methoxybenzyloxymethyl)-2,4-dimethylhex-5-enyloxy]-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

1.2: 0.271 g / KBEt₃H / diethyl ether / 0.5 h / -78 °C

2.1: 74 percent / i-Pr₂NEt / CH₂Cl₂ / 192 h / 20 °C

3.1: DIBAL-H / tetrahydrofuran / 0.5 h / -78 °C

4.1: NaHMDS / tetrahydrofuran; diethyl ether / 4 h / 0 °C

4.2: 0.106 g / diethyl ether; tetrahydrofuran / 0.42 h / 0 °C

With 2,6-dimethylpyridine; sodium hexamethyldisilazane; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1.2: Cram-Felkin-Nguyen reduction / 4.2: Wittig reaction;
DOI:10.1016/S0040-4020(02)00723-8