(1S,2R,4R)-2-[(E)-3-(tert-butyldiphenylsiloxy)-1-methyl-1-propenyl]-5-[3-(methoxymethoxy)propyl]-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-ol

Base Information

Chemical Name:(1S,2R,4R)-2-[(E)-3-(tert-butyldiphenylsiloxy)-1-methyl-1-propenyl]-5-[3-(methoxymethoxy)propyl]-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-ol
CAS No.:607406-41-7
Molecular Formula:C₃₅H₅₀O₄Si
Molecular Weight:562.865
Hs Code.:

Synonyms:(1S,2R,4R)-2-[(E)-3-(tert-butyldiphenylsiloxy)-1-methyl-1-propenyl]-5-[3-(methoxymethoxy)propyl]-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-ol

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Chemical Property of (1S,2R,4R)-2-[(E)-3-(tert-butyldiphenylsiloxy)-1-methyl-1-propenyl]-5-[3-(methoxymethoxy)propyl]-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-ol

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Technology Process of (1S,2R,4R)-2-[(E)-3-(tert-butyldiphenylsiloxy)-1-methyl-1-propenyl]-5-[3-(methoxymethoxy)propyl]-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-ol

There total 8 articles about (1S,2R,4R)-2-[(E)-3-(tert-butyldiphenylsiloxy)-1-methyl-1-propenyl]-5-[3-(methoxymethoxy)propyl]-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-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: 78.0%

: 173044-28-5
(E)-2-bromo-4-(tert-butyldiphenylsilyloxy)-2-butene

: 607406-40-6
(1S,4R)-5-[3-(methoxymethoxy)propyl]-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-one

: 607405-74-3
(3aR,6R,7S,7aR)-7-[(tert-butyldiphenylsilyloxy)methyl]-3,3a,4,6,7,7a-hexahydro-7a-[3-(methoxymethoxy)propyl]-2,3,3,6-tetramethyl-5H-inden-5-one

: 607406-41-7
(1S,2R,4R)-2-[(E)-3-(tert-butyldiphenylsiloxy)-1-methyl-1-propenyl]-5-[3-(methoxymethoxy)propyl]-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-ol

Guidance literature:: (E)-2-bromo-4-(tert-butyldiphenylsilyloxy)-2-butene; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.25h;

(1S,4R)-5-[3-(methoxymethoxy)propyl]-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-one; In tetrahydrofuran; pentane; at -78 - 20 ℃;
DOI:10.1021/jo0301346

Reference yield:

: (1S,4S,5R)-4,7,7-Trimethyl-5-(tetrahydro-pyran-2-yloxy)-bicyclo[2.2.1]heptan-2-one

: 607406-41-7
(1S,2R,4R)-2-[(E)-3-(tert-butyldiphenylsiloxy)-1-methyl-1-propenyl]-5-[3-(methoxymethoxy)propyl]-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0 - 20 °C

1.2: 78 percent / tetrahydrofuran; toluene / 4.75 h / 0 - 20 °C

2.1: 89 percent / lithium chloride / Pd(PPh₃)2Cl₂ / dimethylformamide / 2 h / 100 °C

3.1: 2,3-dimethyl-2-butene; BH₃-THF complex / tetrahydrofuran / 2 h / 0 °C

3.2: 87 percent / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 1.5 h / 0 - 20 °C

4.1: 91 percent / diisopropylethylamine / CH₂Cl₂ / 0 - 20 °C

5.1: 100 percent / p-toluenesulfonic acid; methanol / 1 h / 20 °C

6.1: 90 percent / 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetrapropylammonium perruthenate / CH₂Cl₂ / 2 h / 20 °C

7.1: tert-butyllithium / tetrahydrofuran; pentane / 0.25 h / -78 °C

7.2: tetrahydrofuran; pentane / 2 h / -78 °C

With methanol; 2,3-Dimethyl-2-butene; borane-THF; 4 A molecular sieve; tert.-butyl lithium; potassium hexamethylsilazane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; lithium chloride; bis-triphenylphosphine-palladium(II) chloride; tetrapropylammonium perruthennate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; pentane;
DOI:10.1021/jo0301346

Reference yield:

: 607406-39-3
(1S,2R,4R)-5-[3-(methoxymethoxy)propyl]-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-ol

: 607406-41-7
(1S,2R,4R)-2-[(E)-3-(tert-butyldiphenylsiloxy)-1-methyl-1-propenyl]-5-[3-(methoxymethoxy)propyl]-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 percent / 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetrapropylammonium perruthenate / CH₂Cl₂ / 2 h / 20 °C

2.1: tert-butyllithium / tetrahydrofuran; pentane / 0.25 h / -78 °C

2.2: tetrahydrofuran; pentane / 2 h / -78 °C

With 4 A molecular sieve; tert.-butyl lithium; 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate; In tetrahydrofuran; dichloromethane; pentane;
DOI:10.1021/jo0301346