{(2R,4R,5S,6R)-4-[(S)-1-(2,5-Dimethoxy-phenyl)-1-hydroxy-ethyl]-2-phenyl-6-vinyl-[1,3]dioxan-5-yl}-methyl-carbamic acid methyl ester

Base Information

Chemical Name:{(2R,4R,5S,6R)-4-[(S)-1-(2,5-Dimethoxy-phenyl)-1-hydroxy-ethyl]-2-phenyl-6-vinyl-[1,3]dioxan-5-yl}-methyl-carbamic acid methyl ester
CAS No.:205868-37-7
Molecular Formula:C₂₅H₃₁NO₇
Molecular Weight:457.524
Hs Code.:

Synonyms:{(2R,4R,5S,6R)-4-[(S)-1-(2,5-Dimethoxy-phenyl)-1-hydroxy-ethyl]-2-phenyl-6-vinyl-[1,3]dioxan-5-yl}-methyl-carbamic acid methyl ester

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Chemical Property of {(2R,4R,5S,6R)-4-[(S)-1-(2,5-Dimethoxy-phenyl)-1-hydroxy-ethyl]-2-phenyl-6-vinyl-[1,3]dioxan-5-yl}-methyl-carbamic acid methyl ester

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Technology Process of {(2R,4R,5S,6R)-4-[(S)-1-(2,5-Dimethoxy-phenyl)-1-hydroxy-ethyl]-2-phenyl-6-vinyl-[1,3]dioxan-5-yl}-methyl-carbamic acid methyl ester

There total 14 articles about {(2R,4R,5S,6R)-4-[(S)-1-(2,5-Dimethoxy-phenyl)-1-hydroxy-ethyl]-2-phenyl-6-vinyl-[1,3]dioxan-5-yl}-methyl-carbamic 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: 70.0%

: 25245-34-5
1-bromo-2,5-dimethoxybenzene

: 205868-35-5
((4R)-acetyl-(2R)-phenyl-(6R)-vinyl-[1,3]dioxane-(5S)-yl)methylcarbamic acid methyl ester

: {(2R,4R,5S,6R)-4-[(R)-1-(2,5-Dimethoxy-phenyl)-1-hydroxy-ethyl]-2-phenyl-6-vinyl-[1,3]dioxan-5-yl}-methyl-carbamic acid methyl ester

: 205868-37-7
{(2R,4R,5S,6R)-4-[(S)-1-(2,5-Dimethoxy-phenyl)-1-hydroxy-ethyl]-2-phenyl-6-vinyl-[1,3]dioxan-5-yl}-methyl-carbamic acid methyl ester

Guidance literature:: With n-butyllithium; In tetrahydrofuran; diethyl ether; at 0 ℃;
DOI:10.1080/07328309808002322

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 205868-37-7
{(2R,4R,5S,6R)-4-[(S)-1-(2,5-Dimethoxy-phenyl)-1-hydroxy-ethyl]-2-phenyl-6-vinyl-[1,3]dioxan-5-yl}-methyl-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / p-TsOH / CH₂Cl₂ / 14 h / Ambient temperature

2: 96 percent / I₂, aq. NaHCO₃ / acetone / 6 h / Ambient temperature

3: 41 percent / n-BuLi / tetrahydrofuran / -60 - 20 °C

4: 78 percent / PDC, Ac₂O / CH₂Cl₂ / 3 h / Ambient temperature

5: tetrahydrofuran / -90 °C

With dipyridinium dichromate; n-butyllithium; iodine; acetic anhydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1080/07328309808002322

Reference yield:

: [(3aR,5S,6S,6aR)-5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methyl-amine

: 205868-37-7
{(2R,4R,5S,6R)-4-[(S)-1-(2,5-Dimethoxy-phenyl)-1-hydroxy-ethyl]-2-phenyl-6-vinyl-[1,3]dioxan-5-yl}-methyl-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 85 percent / K₂CO₃ / acetone / 3 h / Heating

2: 70 percent / CH₃CO₂H, H₂O / methanol / 14 h / 55 °C

3: 98 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

4: 97 percent / NaI / butan-2-one / 15 h / 70 °C

5: 98 percent / ZnCl₂ / CH₂Cl₂ / 12 h / Ambient temperature

6: 94 percent / p-TsOH / CH₂Cl₂ / 14 h / Ambient temperature

7: 96 percent / I₂, aq. NaHCO₃ / acetone / 6 h / Ambient temperature

8: 41 percent / n-BuLi / tetrahydrofuran / -60 - 20 °C

9: 78 percent / PDC, Ac₂O / CH₂Cl₂ / 3 h / Ambient temperature

10: tetrahydrofuran / -90 °C

With dipyridinium dichromate; n-butyllithium; water; iodine; acetic anhydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; sodium iodide; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; acetone; butanone;
DOI:10.1080/07328309808002322