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

Base Information

• Chemical Name: (4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-ol
• CAS No.: 688753-68-6
• Molecular Formula: C₃₇H₆₀O₇Si₂
• Molecular Weight: 673.05

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

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

Chemical Property:

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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-ol

There total 8 articles about (4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-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: 74.0%

(4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2E-enal (688753-67-5) + allylmagnesium bromide (1730-25-2) → (4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-ol (688753-68-6) + (4S,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-ol

Guidance literature:

allylmagnesium bromide; With B-chlorodiisopinocampheylborane; In diethyl ether; cooling;

(4R,5S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-4,6-bis(methoxymethoxy)-oct-2E-enal; In diethyl ether; at -78 ℃; for 3h;

DOI:10.1016/j.tet.2004.02.003

Reference yield:

2-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanone (115043-29-3) → (4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-ol (688753-68-6)

Guidance literature:

Multi-step reaction with 8 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

With lead(IV) acetate; 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:

(1R,2S,3S,4S)-2-(tert-butyldimethylsilyloxy)-4-(tert-butyldiphenylsilyloxy)-1-((4S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-1,3-diol (637020-29-2) → (4R,7R,8S,9S,10S)-8-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7,9-bis(methoxymethoxy)-undeca-1,5E-dien-4-ol (688753-68-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 72 percent / DIPEA / CH₂Cl₂ / 96 h / Heating

2.1: 70 percent / pyridinium p-toluenesulfonate / methanol; H₂O / 20 °C

3.1: Pb(OAc)4 / CH₂Cl₂ / 1 h / 20 °C

4.1: 594 mg / DIPEA; LiCl / acetonitrile / 20 °C

5.1: 82 percent / DIBAL / toluene; hexane / 4 h / 0 °C

6.1: 90 percent / PCC; celite / CH₂Cl₂ / 1.5 h / 20 °C

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

7.2: 74 percent / diethyl ether / 3 h / -78 °C

With lead(IV) acetate; Celite; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; 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

upstream raw materials:

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

allylmagnesium bromide

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

(1R,2S,3S,4S)-2-(tert-butyldimethylsilyloxy)-4-(tert-butyldiphenylsilyloxy)-1-((4S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-1,3-diol

Downstream raw materials:

(+)-anamarine

(6R)-6-[(3R,4S,5S,6S)-4-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-3,5-bis(methoxymethoxy)-hept-1-enyl]-5,6-dihydropyran-2-one

(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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