(E)-3-{(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

Base Information

Chemical Name:(E)-3-{(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester
CAS No.:169895-50-5
Molecular Formula:C₃₆H₅₂O₇Si
Molecular Weight:624.89
Hs Code.:

(E)-3-{(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

Synonyms:(E)-3-{(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

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Chemical Property of (E)-3-{(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

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Technology Process of (E)-3-{(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

There total 10 articles about (E)-3-{(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester 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:

: 100-39-0
benzyl bromide

: 169895-50-5
(E)-3-{(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 98 percent / KH / tetrahydrofuran / 2 h / Ambient temperature

2: 100 percent / HCl / methanol / 5 h / Ambient temperature

3: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 1.5 h, 2.) DMF, rt, 12 h

4: 99 percent / imidazole / dimethylformamide / 2 h / 0 °C

5: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C to rt

6: 91 percent / benzene / 1 h / Heating

7: 87 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

8: (+)-DET, Ti(i-PrO)4, t-BuO₂H, 4 Angstroem MS / CH₂Cl₂; 2,2,4-trimethyl-pentane / 12 h / -20 °C

9: SO₃*py, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / Ambient temperature

10: benzene / 11 h / Ambient temperature

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 Angstroem MS; potassium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; triethylamine; triphenylphosphine; cesium fluoride; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo9807619

Reference yield:

: 132375-60-1
3-((3aR,4R,6R,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-propan-1-ol

: 169895-50-5
(E)-3-{(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 98 percent / KH / tetrahydrofuran / 2 h / Ambient temperature

2: 100 percent / HCl / methanol / 5 h / Ambient temperature

3: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 1.5 h, 2.) DMF, rt, 12 h

4: 99 percent / imidazole / dimethylformamide / 2 h / 0 °C

5: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C to rt

6: 91 percent / benzene / 1 h / Heating

7: 87 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

8: (+)-DET, Ti(i-PrO)4, t-BuO₂H, 4 Angstroem MS / CH₂Cl₂; 2,2,4-trimethyl-pentane / 12 h / -20 °C

9: SO₃*py, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / Ambient temperature

10: benzene / 11 h / Ambient temperature

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 Angstroem MS; potassium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; triethylamine; triphenylphosphine; cesium fluoride; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo9807619

Reference yield:

: 169895-74-3
(3aR,4R,6R,7aS)-4-Allyl-6-(3-benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

: 169895-50-5
(E)-3-{(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / HCl / methanol / 5 h / Ambient temperature

2: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 1.5 h, 2.) DMF, rt, 12 h

3: 99 percent / imidazole / dimethylformamide / 2 h / 0 °C

4: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C to rt

5: 91 percent / benzene / 1 h / Heating

6: 87 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

7: (+)-DET, Ti(i-PrO)4, t-BuO₂H, 4 Angstroem MS / CH₂Cl₂; 2,2,4-trimethyl-pentane / 12 h / -20 °C

8: SO₃*py, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / Ambient temperature

9: benzene / 11 h / Ambient temperature

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 Angstroem MS; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; triethylamine; triphenylphosphine; cesium fluoride; In methanol; 2,2,4-trimethylpentane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo9807619