(2E,4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2-en-1-ol

Base Information

Chemical Name:(2E,4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2-en-1-ol
CAS No.:688753-66-4
Molecular Formula:C₃₄H₅₆O₇Si₂
Molecular Weight:632.985
Hs Code.:

Synonyms:(2E,4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2-en-1-ol

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Chemical Property of (2E,4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2-en-1-ol

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Technology Process of (2E,4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2-en-1-ol

There total 5 articles about (2E,4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2-en-1-ol 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: 82.0%

: 688753-65-3
ethyl (2E,4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2-enoate

: 688753-66-4
(2E,4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; toluene; at 0 ℃; for 4h;
DOI:10.1016/j.tet.2004.02.003

Reference yield:

: 115043-29-3
2-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanone

: 688753-66-4
(2E,4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: chlorodicyclohexylborane; Et₃N / diethyl ether / 0 °C

1.2: diethyl ether / 5 h / -78 - 0 °C

1.3: 75 percent / LiBH₄ / diethyl ether / 2 h / -78 °C

2.1: 72 percent / DIPEA / CH₂Cl₂ / 96 h / Heating

3.1: 70 percent / pyridinium p-toluenesulfonate / methanol; H₂O / 20 °C

4.1: Pb(OAc)4 / CH₂Cl₂ / 1 h / 20 °C

5.1: 594 mg / DIPEA; LiCl / acetonitrile / 20 °C

6.1: 82 percent / DIBAL / toluene; hexane / 4 h / 0 °C

With lead(IV) acetate; dicyclohexylboron chloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In methanol; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile;
DOI:10.1016/j.tet.2004.02.003

Reference yield:

: 3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2,4-bis-methoxymethoxy-hexanal

: 688753-66-4
(2E,4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 594 mg / DIPEA; LiCl / acetonitrile / 20 °C

2: 82 percent / DIBAL / toluene; hexane / 4 h / 0 °C

With diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; In hexane; toluene; acetonitrile;
DOI:10.1016/j.tet.2004.02.003