methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-hydroxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate

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Chemical Name:methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-hydroxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate
CAS No.:667421-81-0
Molecular Formula:C₂₅H₃₂O₅Si
Molecular Weight:440.612
Hs Code.:

Synonyms:methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-hydroxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate

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Chemical Property of methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-hydroxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate

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Technology Process of methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-hydroxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate

There total 8 articles about methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-hydroxypropyl](2S,3R)oxiran-2-yl}prop-2-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: 82.0%

: 667421-86-5
methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-triethylsiloxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate

: 667421-81-0
methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-hydroxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate

Guidance literature:: With camphor-10-sulfonic acid; In methanol; at 0 ℃; for 0.0833333h;
DOI:10.3987/com-03-9952

Reference yield:

: 667421-82-1
methyl (3S)-4-tert-butyldiphenylsiloxy-3-triethylsiloxybutanoate

: 667421-81-0
methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-hydroxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: DIBAL-H / toluene / 1 h / -78 °C

1.2: 94 percent / benzene / 8 h / 20 °C

2.1: 95 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

3.1: 90 percent / Ti(Oi-Pr)4; (-)-diethyl-D-tartrate; TBHP / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

4.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C

4.2: 79 percent / benzene / 8 h / 20 °C

5.1: 82 percent / CSA / methanol / 0.08 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In methanol; 2,2,4-trimethylpentane; dichloromethane; toluene; 1.2: Wittig reaction / 3.1: Sharpless asymmetric epoxydation / 4.2: Wittig reaction;
DOI:10.3987/com-03-9952

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 667421-81-0
methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-hydroxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: imidazole / dimethylformamide / 0.33 h / 20 °C

1.2: 95 percent / imidazole / dimethylformamide / 0.33 h / 0 °C

2.1: DIBAL-H / toluene / 1 h / -78 °C

2.2: 94 percent / benzene / 8 h / 20 °C

3.1: 95 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

4.1: 90 percent / Ti(Oi-Pr)4; (-)-diethyl-D-tartrate; TBHP / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

5.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C

5.2: 79 percent / benzene / 8 h / 20 °C

6.1: 82 percent / CSA / methanol / 0.08 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In methanol; 2,2,4-trimethylpentane; dichloromethane; N,N-dimethyl-formamide; toluene; 2.2: Wittig reaction / 4.1: Sharpless asymmetric epoxydation / 5.2: Wittig reaction;
DOI:10.3987/com-03-9952