methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenylpent-4-enoate

Base Information

Chemical Name:methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenylpent-4-enoate
CAS No.:475503-86-7
Molecular Formula:C₁₉H₃₀O₃Si
Molecular Weight:334.531
Hs Code.:

Synonyms:methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenylpent-4-enoate

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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)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenylpent-4-enoate

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Technology Process of methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenylpent-4-enoate

There total 4 articles about methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenylpent-4-enoate 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: 85.0%

: 69739-34-0
t-butyldimethylsiyl triflate

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

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

Guidance literature:: With 2,6-dimethylpyridine; dmap; In dichloromethane; at 20 ℃; for 2.5h;
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

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

Guidance literature:: Multi-step reaction with 4 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

With 2,6-dimethylpyridine; dmap; sodium hydroxide; thionyl chloride; tin(IV) chloride; 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:

: 475503-84-5
(2S,3R)-2-hydroxy-4-methyl-3-phenylpent-4-enoic acid

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

Guidance literature:: Multi-step reaction with 2 steps

1: 79 percent / SOCl₂ / methanol / 4 h / Heating

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

With 2,6-dimethylpyridine; dmap; thionyl chloride; In methanol; dichloromethane;
DOI:10.1002/1099-0690(200209)2002:17<2905::AID-EJOC2905>3.0.CO;2-3