(2E,5R,7R,8R)-3-bromo-1-tert-butyldiphenylsilyloxy-5,8-bis-(tertbutyldimethylsilyloxy)-7-(2-trimethylsilylethoxymethoxy)non-2-ene

Base Information

Chemical Name:(2E,5R,7R,8R)-3-bromo-1-tert-butyldiphenylsilyloxy-5,8-bis-(tertbutyldimethylsilyloxy)-7-(2-trimethylsilylethoxymethoxy)non-2-ene
CAS No.:884345-46-4
Molecular Formula:C₄₃H₇₇BrO₅Si₄
Molecular Weight:866.327
Hs Code.:

Synonyms:(2E,5R,7R,8R)-3-bromo-1-tert-butyldiphenylsilyloxy-5,8-bis-(tertbutyldimethylsilyloxy)-7-(2-trimethylsilylethoxymethoxy)non-2-ene

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Chemical Property of (2E,5R,7R,8R)-3-bromo-1-tert-butyldiphenylsilyloxy-5,8-bis-(tertbutyldimethylsilyloxy)-7-(2-trimethylsilylethoxymethoxy)non-2-ene

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Technology Process of (2E,5R,7R,8R)-3-bromo-1-tert-butyldiphenylsilyloxy-5,8-bis-(tertbutyldimethylsilyloxy)-7-(2-trimethylsilylethoxymethoxy)non-2-ene

There total 14 articles about (2E,5R,7R,8R)-3-bromo-1-tert-butyldiphenylsilyloxy-5,8-bis-(tertbutyldimethylsilyloxy)-7-(2-trimethylsilylethoxymethoxy)non-2-ene 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: 97.0%

: (2E,5R,7R,8R)-1-tert-butyldiphenylsilyloxy-5,8-bis-(tert-butyldimethylsilyloxy)-3-tributylstannyl-7-(2-trimethylsilylethoxymethoxy)non-2-ene

: 884345-46-4
(2E,5R,7R,8R)-3-bromo-1-tert-butyldiphenylsilyloxy-5,8-bis-(tertbutyldimethylsilyloxy)-7-(2-trimethylsilylethoxymethoxy)non-2-ene

Guidance literature:: With N-Bromosuccinimide; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1039/c7ob00076f

Reference yield:

: 38996-24-6
(4R,5R)-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone

: 884345-46-4
(2E,5R,7R,8R)-3-bromo-1-tert-butyldiphenylsilyloxy-5,8-bis-(tertbutyldimethylsilyloxy)-7-(2-trimethylsilylethoxymethoxy)non-2-ene

Guidance literature:: Multi-step reaction with 10 steps

1: 95 percent / iPr₂NEt; DMAP / 72 h

2: HCl; AlMe₃

3: imidazole

4: 87 percent / DIBAL-H / tetrahydrofuran / -78 °C

5: Zn / -78 - -15 °C

6: PPh₃; DIAD / tetrahydrofuran

7: NaOH / methanol

8: 94 percent / 2,6-lutidine

9: 92 percent / nBuLi / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium hydroxide; n-butyllithium; di-isopropyl azodicarboxylate; trimethylaluminum; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; In tetrahydrofuran; methanol; 6: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2006.01.097

Reference yield:

: 884345-43-1
(3R,4R)-4-tert-butyldimethylsilyloxy-3-(2-trimethylsilylethoxymethoxy)pentanal

: 884345-46-4
(2E,5R,7R,8R)-3-bromo-1-tert-butyldiphenylsilyloxy-5,8-bis-(tertbutyldimethylsilyloxy)-7-(2-trimethylsilylethoxymethoxy)non-2-ene

Guidance literature:: Multi-step reaction with 6 steps

1: Zn / -78 - -15 °C

2: PPh₃; DIAD / tetrahydrofuran

3: NaOH / methanol

4: 94 percent / 2,6-lutidine

5: 92 percent / nBuLi / -78 °C

With 2,6-dimethylpyridine; sodium hydroxide; n-butyllithium; di-isopropyl azodicarboxylate; triphenylphosphine; zinc; In tetrahydrofuran; methanol; 2: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2006.01.097