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

Base Information

Chemical Name:(2S,3R,4S)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone
CAS No.:475503-91-4
Molecular Formula:C₁₈H₂₈O₃Si
Molecular Weight:320.504
Hs Code.:

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

Suppliers and Price of (2S,3R,4S)-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,4S)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone

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

There total 10 articles about (2S,3R,4S)-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: 23.0%

: 475503-90-3
ethyl (2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-4-methyl-3-phenylpentanoate

: 475503-91-4
(2S,3R,4S)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone

Guidance literature:: ethyl (2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-4-methyl-3-phenylpentanoate; With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;

With sodium hydrogencarbonate; In ethanol; Heating;

With sodium tetrahydroborate; In methanol; at 0 ℃; Further stages.;
DOI:10.1002/1099-0690(200209)2002:17<2905::AID-EJOC2905>3.0.CO;2-3

Reference yield: 20.0%

: 1027145-18-1
(2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-3-phenyl-pentanoic acid ethyl ester

: 475503-91-4
(2S,3R,4S)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone

: 475503-90-3
ethyl (2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-4-methyl-3-phenylpentanoate

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.416667h;
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

: 475503-91-4
(2S,3R,4S)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone

Guidance literature:: Multi-step reaction with 8 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: DMSO; oxalyl chloride; NEt₃ / CH₂Cl₂ / 0.33 h / -78 °C

7.1: NaHCO₃ / 3 h / Heating

8.1: 20 percent / NaBH₄ / methanol / 0.42 h / 0 °C

With 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; oxalyl dichloride; tin(IV) chloride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; dichloromethane; 1.1: Whitesell ene reaction / 6.1: Swern oxidation;
DOI:10.1002/1099-0690(200209)2002:17<2905::AID-EJOC2905>3.0.CO;2-3