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

Base Information

• Chemical Name: methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-triethylsiloxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate
• CAS No.: 667421-86-5
• Molecular Formula: C₃₁H₄₆O₅Si₂
• Molecular Weight: 554.874

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

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

Chemical Property:

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

There total 9 articles about methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-triethylsiloxypropyl](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: 79.0%

methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) + {3-[(2S)-3-tert-butyldiphenylsiloxy-2-triethylsiloxypropyl](2S,3R)oxiran-2-yl}-methanol (667421-85-4) → methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-triethylsiloxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate (667421-86-5)

Guidance literature:

{3-[(2S)-3-tert-butyldiphenylsiloxy-2-triethylsiloxypropyl](2S,3R)oxiran-2-yl}-methanol; With pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine; In dichloromethane; at 20 ℃; for 2h;

methyl (triphenylphosphoranylidene)acetate; In benzene; at 20 ℃; for 8h;

DOI:10.3987/com-03-9952

Reference yield:

triethylsilyl chloride (994-30-9) → methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-triethylsiloxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate (667421-86-5)

Guidance literature:

Multi-step reaction with 5 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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In 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

Reference yield:

methyl (3S)-4-tert-butyldiphenylsiloxy-3-triethylsiloxybutanoate (667421-82-1) → methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-triethylsiloxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate (667421-86-5)

Guidance literature:

Multi-step reaction with 4 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In 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

upstream raw materials:

methyl (triphenylphosphoranylidene)acetate

{3-[(2S)-3-tert-butyldiphenylsiloxy-2-triethylsiloxypropyl](2S,3R)oxiran-2-yl}-methanol

triethylsilyl chloride

(3S)-4-(tert-butyldiphenylsilyl)oxy-3-(triethylsilyl)oxy-butyraldehyde

Downstream raw materials:

(1S,2S)-{1-[(4S)-2-(4-methoxyphenyl)1,3-dioxan-4-yl]-3-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-2-phenylmethoxymethylpropoxy}-2-methoxyethoxymethane

(3S,4S,5S)-5-{[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]methyl}-3,6-bis(methanesulfonyloxy)-4-(2-methoxyethoxymethoxy)hexyl 2,2-dimethylpropanoate

Acetic acid (R)-6-benzyloxy-1-{2-[(2S,3aR,5S,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-ethyl}-5-triethylsilanyloxy-hex-2-ynyl ester

(3S,4S,5S)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-3-hydroxy-4-(2-methoxyethoxymethoxy)-5-(phenylmethoxymethyl)hexyl 2,2-dimethylpropanoate

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