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

Base Information

Chemical Name:(4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2E-enal
CAS No.:688753-67-5
Molecular Formula:C₃₄H₅₄O₇Si₂
Molecular Weight:630.97
Hs Code.:

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

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

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

There total 6 articles about (4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2E-enal 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: 90.0%

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

: 688753-67-5
(4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2E-enal

Guidance literature:: With Celite; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 1.5h;
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

: 688753-67-5
(4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2E-enal

Guidance literature:: Multi-step reaction with 7 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

7.1: 90 percent / PCC; celite / CH₂Cl₂ / 1.5 h / 20 °C

With lead(IV) acetate; Celite; dicyclohexylboron chloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; 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

: 688753-67-5
(4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2E-enal

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 90 percent / PCC; celite / CH₂Cl₂ / 1.5 h / 20 °C

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