1-(S)-((2R,4S,5S,6R)-5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxan-4-yl)-1-(4-bromo-2,5-dimethoxyphenyl)ethanol

Base Information

Chemical Name:1-(S)-((2R,4S,5S,6R)-5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxan-4-yl)-1-(4-bromo-2,5-dimethoxyphenyl)ethanol
CAS No.:205816-29-1
Molecular Formula:C₂₉H₃₁BrO₆
Molecular Weight:555.466
Hs Code.:

Synonyms:1-(S)-((2R,4S,5S,6R)-5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxan-4-yl)-1-(4-bromo-2,5-dimethoxyphenyl)ethanol

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Chemical Property of 1-(S)-((2R,4S,5S,6R)-5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxan-4-yl)-1-(4-bromo-2,5-dimethoxyphenyl)ethanol

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Technology Process of 1-(S)-((2R,4S,5S,6R)-5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxan-4-yl)-1-(4-bromo-2,5-dimethoxyphenyl)ethanol

There total 7 articles about 1-(S)-((2R,4S,5S,6R)-5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxan-4-yl)-1-(4-bromo-2,5-dimethoxyphenyl)ethanol 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: 80.0%

: 2674-34-2
1,4-dibromo-2,5-dimethoxybenzene

: 205816-27-9
1-((2R,4R,5S,6R)-5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxan-4-yl)ethanone

: 1-(R)-((2R,4S,5S,6R)-5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxan-4-yl)-1-(4-bromo-2,5-dimethoxyphenyl)ethanol

: 205816-29-1
1-(S)-((2R,4S,5S,6R)-5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxan-4-yl)-1-(4-bromo-2,5-dimethoxyphenyl)ethanol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; 1.) -50 deg C -> 0 deg C, 2.) 0 deg C, 40 min;
DOI:10.1080/07328309808002320

Reference yield:

: 100-52-7
benzaldehyde

: 205816-29-1
1-(S)-((2R,4S,5S,6R)-5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxan-4-yl)-1-(4-bromo-2,5-dimethoxyphenyl)ethanol

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / CF₃CO₂H / CHCl₃ / 7 h / Heating

2: 68 percent / CrO₃/Py, Ac₂O / CH₂Cl₂ / 0.17 h

3: 76 percent / tetrahydrofuran / 16 h / Ambient temperature

4: 71 percent / DMSO, PDCP, Et₃N / CH₂Cl₂ / 2.5 h / Ambient temperature

5: 80 percent / n-BuLi / tetrahydrofuran / 1.) -50 deg C -> 0 deg C, 2.) 0 deg C, 40 min

With n-butyllithium; chromium trioxide-pyridine complex; acetic anhydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1080/07328309808002320

Reference yield:

: 4-benzyloxy-5-vinyl-(3R,4S,5R)-tetrahydro-2,3-furandiol

: 205816-29-1
1-(S)-((2R,4S,5S,6R)-5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxan-4-yl)-1-(4-bromo-2,5-dimethoxyphenyl)ethanol

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / NaBH₄ / ethanol / 48 h / Ambient temperature

2: 80 percent / CF₃CO₂H / CHCl₃ / 7 h / Heating

3: 68 percent / CrO₃/Py, Ac₂O / CH₂Cl₂ / 0.17 h

4: 76 percent / tetrahydrofuran / 16 h / Ambient temperature

5: 71 percent / DMSO, PDCP, Et₃N / CH₂Cl₂ / 2.5 h / Ambient temperature

6: 80 percent / n-BuLi / tetrahydrofuran / 1.) -50 deg C -> 0 deg C, 2.) 0 deg C, 40 min

With sodium tetrahydroborate; n-butyllithium; chromium trioxide-pyridine complex; acetic anhydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; chloroform;
DOI:10.1080/07328309808002320