(E)-(4R,6R,9S)-10-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-6,9-dimethyl-deca-1,7-dien-4-ol

Base Information

• Chemical Name: (E)-(4R,6R,9S)-10-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-6,9-dimethyl-deca-1,7-dien-4-ol
• CAS No.: 266675-84-7
• Molecular Formula: C₃₈H₅₂O₄Si
• Molecular Weight: 600.914

Synonyms:(E)-(4R,6R,9S)-10-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-6,9-dimethyl-deca-1,7-dien-4-ol

Chemical Property of (E)-(4R,6R,9S)-10-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-6,9-dimethyl-deca-1,7-dien-4-ol

Chemical Property:

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Technology Process of (E)-(4R,6R,9S)-10-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-6,9-dimethyl-deca-1,7-dien-4-ol

There total 11 articles about (E)-(4R,6R,9S)-10-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-6,9-dimethyl-deca-1,7-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:

(E)-(3R,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-3-[2-(4-methoxy-benzyloxy)-ethyl]-3,6-dimethyl-hept-4-enal (266675-82-5) + allylmagnesium bromide (1730-25-2) → (E)-(4R,6R,9S)-10-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-6,9-dimethyl-deca-1,7-dien-4-ol (266675-84-7) + (E)-(4S,6R,9S)-10-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-6,9-dimethyl-deca-1,7-dien-4-ol

Guidance literature:

With (+)-B-methoxydiisocamphenylborane; In diethyl ether; at -78 ℃; Title compound not separated from byproducts.;

DOI:10.1021/ol9904085

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (E)-(4R,6R,9S)-10-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-6,9-dimethyl-deca-1,7-dien-4-ol (266675-84-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: TfOH / diethyl ether / 20 °C

2.1: nBuLi / tetrahydrofuran / -78 - 20 °C

3.1: tetrahydrofuran / -45 °C

4.1: LiAlH₄ / diethyl ether / 0 °C

5.1: MnO₂ / CH₂Cl₂

5.2: 74 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 °C

6.1: 86 percent / LiBH₄; MeOH / diethyl ether

7.1: 84 percent / Et₃N; DMAP / CH₂Cl₂

8.1: 89 percent / p-xylene / 100 °C

9.1: LiAl(nBu)iBu₂H / tetrahydrofuran / 20 °C

10.1: (+)-(lpc)2BOCH₃ / diethyl ether / -78 °C

With methanol; dmap; manganese(IV) oxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; lithium n-butyldiisobutylaluminum hydride; trifluorormethanesulfonic acid; triethylamine; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; diethyl ether; dichloromethane; para-xylene; 1.1: Substitution / 2.1: Substitution / 3.1: Addition / 4.1: Reduction / 5.1: Oxidation / 5.2: Evans aldolization / 6.1: cleavage / 7.1: silylation / 8.1: Eschenmoser-Claisen rearrangement / 9.1: Reduction / 10.1: Grignard reaction;

DOI:10.1021/ol9904085

Reference yield:

1-but-3-ynyloxymethyl-4-methoxy-benzene (218434-90-3) → (E)-(4R,6R,9S)-10-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-6,9-dimethyl-deca-1,7-dien-4-ol (266675-84-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: nBuLi / tetrahydrofuran / -78 - 20 °C

2.1: tetrahydrofuran / -45 °C

3.1: LiAlH₄ / diethyl ether / 0 °C

4.1: MnO₂ / CH₂Cl₂

4.2: 74 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 °C

5.1: 86 percent / LiBH₄; MeOH / diethyl ether

6.1: 84 percent / Et₃N; DMAP / CH₂Cl₂

7.1: 89 percent / p-xylene / 100 °C

8.1: LiAl(nBu)iBu₂H / tetrahydrofuran / 20 °C

9.1: (+)-(lpc)2BOCH₃ / diethyl ether / -78 °C

With methanol; dmap; manganese(IV) oxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; lithium n-butyldiisobutylaluminum hydride; triethylamine; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; diethyl ether; dichloromethane; para-xylene; 1.1: Substitution / 2.1: Addition / 3.1: Reduction / 4.1: Oxidation / 4.2: Evans aldolization / 5.1: cleavage / 6.1: silylation / 7.1: Eschenmoser-Claisen rearrangement / 8.1: Reduction / 9.1: Grignard reaction;

DOI:10.1021/ol9904085

upstream raw materials:

(E)-(3R,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-3-[2-(4-methoxy-benzyloxy)-ethyl]-3,6-dimethyl-hept-4-enal

allylmagnesium bromide

O-(4-methoxybenzyl)-trichloroacetimidate

1-but-3-ynyloxymethyl-4-methoxy-benzene

Downstream raw materials:

tert-Butyl-{(E)-(2S,5R,7R)-5-[2-(4-methoxy-benzyloxy)-ethyl]-7-methoxymethoxy-2,5-dimethyl-deca-3,9-dienyloxy}-diphenyl-silane

(E)-(3S,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-3-methoxymethoxy-5,8-dimethyl-nona-6,8-dienal

1-Methoxy-4-[(E)-(3R,5R)-5-methoxymethoxy-3-methyl-3-((E)-3-methyl-buta-1,3-dienyl)-8-nitro-oct-7-enyloxymethyl]-benzene

(E)-(4S,6R)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-4-methoxymethoxy-6,9-dimethyl-deca-7,9-diene-1,2-diol

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