3'-methyl-2'-butenyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate

Base Information

Chemical Name:3'-methyl-2'-butenyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate
CAS No.:263369-08-0
Molecular Formula:C₂₉H₄₀O₄Si
Molecular Weight:480.72
Hs Code.:

Synonyms:3'-methyl-2'-butenyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate

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Chemical Property of 3'-methyl-2'-butenyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate

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Technology Process of 3'-methyl-2'-butenyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate

There total 9 articles about 3'-methyl-2'-butenyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate 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: 79.0%

: 556-82-1
3-methyl-2-buten-1-ol

: 263369-07-9
methyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate

: 263369-08-0
3'-methyl-2'-butenyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate

Guidance literature:: With 1-chloro-3-hydroxy-1,1,3,3-tetrabutyldistannoxane; In toluene; for 15h; Heating;
DOI:10.1002/(SICI)1099-0690(200001)2000:2<357::AID-EJOC357>3.0.CO;2-N

Reference yield:

: 29736-80-9
3,5-dioxohexanoic acid methyl ester

: 263369-08-0
3'-methyl-2'-butenyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: NaH; tert-butyllithium / tetrahydrofuran; pentane / 0 °C

1.2: 70 percent / tetrahydrofuran; pentane / 2 h / 0 °C

2.1: 44 percent / DIBAL / tetrahydrofuran; toluene / 0.5 h / -78 °C

3.1: diethylmethoxyborane / tetrahydrofuran; methanol / 0.75 h / -78 °C

3.2: 90 percent / sodium borohydride / methanol; tetrahydrofuran / 5 h / -78 °C

4.1: 75 percent / Raney nickel / methanol / 6 h

5.1: 83 percent / zinc chloride; 4 Angstroem molecular sieves / tetrahydrofuran / 4 h / Heating

6.1: 87 percent / imidazole / dimethylformamide / 48 h / 20 °C

7.1: 87 percent / DIBAL / CH₂Cl₂; toluene / 0.5 h / -78 °C

8.1: 80 percent / acetonitrile / 12.5 h / Heating

9.1: 79 percent / 1-hydroxy-3-chlorotetrabutyldistannoxane / toluene / 15 h / Heating

With 1H-imidazole; 4 A molecular sieve; diethyl methoxy borane; tert.-butyl lithium; nickel; sodium hydride; diisobutylaluminium hydride; 1-chloro-3-hydroxy-1,1,3,3-tetrabutyldistannoxane; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; 1.1: deprotonation / 1.2: Substitution / 2.1: Hydrogenation / 3.1: boronation / 3.2: Hydrogenation / 4.1: desulfurization / 5.1: Cyclization / 6.1: Etherification / 7.1: Hydrogenation / 8.1: Ring cleavage / 9.1: Esterification;
DOI:10.1002/(SICI)1099-0690(200001)2000:2<357::AID-EJOC357>3.0.CO;2-N

Reference yield:

: 121843-07-0
(4R,6R)-4-hydroxy-6-methyltetrahydro-2H-pyran-2-one

: 263369-08-0
3'-methyl-2'-butenyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / imidazole / dimethylformamide / 48 h / 20 °C

2: 87 percent / DIBAL / CH₂Cl₂; toluene / 0.5 h / -78 °C

3: 80 percent / acetonitrile / 12.5 h / Heating

4: 79 percent / 1-hydroxy-3-chlorotetrabutyldistannoxane / toluene / 15 h / Heating

With 1H-imidazole; diisobutylaluminium hydride; 1-chloro-3-hydroxy-1,1,3,3-tetrabutyldistannoxane; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Etherification / 2: Hydrogenation / 3: Ring cleavage / 4: Esterification;
DOI:10.1002/(SICI)1099-0690(200001)2000:2<357::AID-EJOC357>3.0.CO;2-N