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

Base Information

Chemical Name:methyl (2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-4-methyl-3-phenylpentanoate
CAS No.:475503-87-8
Molecular Formula:C₁₉H₃₂O₄Si
Molecular Weight:352.546
Hs Code.:

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

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

There total 5 articles about methyl (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: 98.0%

: 475503-86-7
methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenylpent-4-enoate

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

Guidance literature:: methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenylpent-4-enoate; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 20 ℃; for 3.5h;

With sodium hydroxide; dihydrogen peroxide; for 0.5h; Further stages.; sonication;
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

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

Guidance literature:: Multi-step reaction with 5 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

With 2,6-dimethylpyridine; dmap; sodium hydroxide; thionyl chloride; tin(IV) chloride; 9-bora-bicyclo[3.3.1]nonane; 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

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

Guidance literature:: Multi-step reaction with 2 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

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