(E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol

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Chemical Name:(E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol
CAS No.:169895-48-1
Molecular Formula:C₃₃H₅₀O₅Si
Molecular Weight:554.842
Hs Code.:

Synonyms:(E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol

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Chemical Property of (E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol

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Technology Process of (E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol

There total 8 articles about (E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol 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: 87.0%

: 169895-47-0
(E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-enoic acid ethyl ester

: 169895-48-1
(E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/jo9807619

Reference yield:

: 100-39-0
benzyl bromide

: 169895-48-1
(E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; hydrogenchloride; potassium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; triphenylphosphine; cesium fluoride; In tetrahydrofuran; methanol; dichloromethane; 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

: 169895-48-1
(E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; hydrogenchloride; potassium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; triphenylphosphine; cesium fluoride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo9807619