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

Base Information

Chemical Name:ethyl (2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-4-methyl-3-phenylpentanoate
CAS No.:475503-90-3
Molecular Formula:C₂₀H₃₄O₄Si
Molecular Weight:366.573
Hs Code.:

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

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

Chemical Property:

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Technology Process of ethyl (2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-4-methyl-3-phenylpentanoate

There total 8 articles about ethyl (2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-4-methyl-3-phenylpentanoate 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: 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

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

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: 36 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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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: DMSO; oxalyl chloride; NEt₃ / CH₂Cl₂ / 0.33 h / -78 °C

4.1: NaHCO₃ / 3 h / Heating

5.1: 36 percent / NaBH₄ / methanol / 0.42 h / 0 °C

With 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; dichloromethane; 3.1: Swern oxidation;
DOI:10.1002/1099-0690(200209)2002:17<2905::AID-EJOC2905>3.0.CO;2-3