(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone

Base Information

Chemical Name:(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone
CAS No.:475503-88-9
Molecular Formula:C₁₈H₂₈O₃Si
Molecular Weight:320.504
Hs Code.:

Synonyms:(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone

Chemical Property:

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Technology Process of (2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone

There total 6 articles about (2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone 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: 96.0%

: 475503-87-8
methyl (2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-4-methyl-3-phenylpentanoate

: 475503-88-9
(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1002/1099-0690(200209)2002:17<2905::AID-EJOC2905>3.0.CO;2-3

Reference yield:

: 768-49-0
(2-methyl-1-propenyl)-benzene

: 475503-88-9
(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone

Guidance literature:: Multi-step reaction with 6 steps

1.1: SnCl₄ / CH₂Cl₂ / 2.5 h / -78 °C

1.2: 81 percent / 19 h / -25 °C

2.1: 90 percent / NaOH / tetrahydrofuran; methanol / 15 h / Heating

3.1: 79 percent / SOCl₂ / methanol / 4 h / Heating

4.1: 85 percent / 2,6-lutidine; DMAP / CH₂Cl₂ / 2.5 h / 20 °C

5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3.5 h / 20 °C

5.2: 98 percent / NaOH; H₂O₂ / 0.5 h / sonication

6.1: 96 percent / TFA / CH₂Cl₂ / 4 h / 20 °C

With 2,6-dimethylpyridine; dmap; sodium hydroxide; thionyl chloride; tin(IV) chloride; 9-bora-bicyclo[3.3.1]nonane; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; 1.1: Whitesell ene reaction;
DOI:10.1002/1099-0690(200209)2002:17<2905::AID-EJOC2905>3.0.CO;2-3

Reference yield:

: 475503-85-6
methyl (2S,3R)-2-hydroxy-4-methyl-3-phenylpent-4-enoate

: 475503-88-9
(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone

Guidance literature:: Multi-step reaction with 3 steps

1.1: 85 percent / 2,6-lutidine; DMAP / CH₂Cl₂ / 2.5 h / 20 °C

2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3.5 h / 20 °C

2.2: 98 percent / NaOH; H₂O₂ / 0.5 h / sonication

3.1: 96 percent / TFA / CH₂Cl₂ / 4 h / 20 °C

With 2,6-dimethylpyridine; dmap; 9-bora-bicyclo[3.3.1]nonane; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1002/1099-0690(200209)2002:17<2905::AID-EJOC2905>3.0.CO;2-3