(4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-yl (E)-3-phenylacrylate

Base Information

Chemical Name:(4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-yl (E)-3-phenylacrylate
CAS No.:688753-69-7
Molecular Formula:C₄₆H₆₆O₈Si₂
Molecular Weight:803.196
Hs Code.:

(4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-yl (E)-3-phenylacrylate

Synonyms:(4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-yl (E)-3-phenylacrylate

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Chemical Property of (4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-yl (E)-3-phenylacrylate

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Technology Process of (4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-yl (E)-3-phenylacrylate

There total 9 articles about (4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-yl (E)-3-phenylacrylate 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: 81.0%

: 102-92-1,17082-09-6
Cinnamoyl chloride

: 688753-68-6
(4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-ol

: 688753-69-7
(4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-yl (E)-3-phenylacrylate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1016/j.tet.2004.02.003

Reference yield:

: 87696-33-1
(S)-2-(O-tert-butyldiphenylsilyloxy)propanal

: 688753-69-7
(4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-yl (E)-3-phenylacrylate

Guidance literature:: Multi-step reaction with 9 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

8.1: (+)-diisopinocampheylboron chloride / diethyl ether / cooling

8.2: 74 percent / diethyl ether / 3 h / -78 °C

9.1: 81 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

With lead(IV) acetate; dmap; Celite; dicyclohexylboron chloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; B-chlorodiisopinocampheylborane; lithium chloride; In methanol; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile;
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

: 688753-69-7
(4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-yl (E)-3-phenylacrylate

Guidance literature:: Multi-step reaction with 9 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

8.1: (+)-diisopinocampheylboron chloride / diethyl ether / cooling

8.2: 74 percent / diethyl ether / 3 h / -78 °C

9.1: 81 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

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