5-((2R,3R,4S,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyltetrahydrofuran-2-yl)benzo[d][1,3]dioxole

Base Information

Chemical Name:5-((2R,3R,4S,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyltetrahydrofuran-2-yl)benzo[d][1,3]dioxole
CAS No.:1296147-83-5
Molecular Formula:C₂₇H₂₈O₅
Molecular Weight:432.516
Hs Code.:

Synonyms:5-((2R,3R,4S,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyltetrahydrofuran-2-yl)benzo[d][1,3]dioxole

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Chemical Property of 5-((2R,3R,4S,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyltetrahydrofuran-2-yl)benzo[d][1,3]dioxole

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Technology Process of 5-((2R,3R,4S,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyltetrahydrofuran-2-yl)benzo[d][1,3]dioxole

There total 31 articles about 5-((2R,3R,4S,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyltetrahydrofuran-2-yl)benzo[d][1,3]dioxole 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: 56.0%

: 1296147-82-4
(1R,2R,3S,4S)-1-(benzo[d][1,3]dioxol-5-yl)-4-(4-(benzyloxy)-3-methoxyphenyl)-2,3-dimethylbutane-1,4-diol

: 1296147-83-5
5-((2R,3R,4S,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyltetrahydrofuran-2-yl)benzo[d][1,3]dioxole

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; for 12h;
DOI:10.1021/acs.joc.5b00945

Reference yield:

: 1296147-82-4
(1R,2R,3S,4S)-1-(benzo[d][1,3]dioxol-5-yl)-4-(4-(benzyloxy)-3-methoxyphenyl)-2,3-dimethylbutane-1,4-diol

: 1072281-38-9
C₂₇H₂₈O₅

: 1296147-83-5
5-((2R,3R,4S,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyltetrahydrofuran-2-yl)benzo[d][1,3]dioxole

: C₂₇H₂₈O₅

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 20 ℃; stereoselective reaction;
DOI:10.3987/COM-10-S(E)88

Reference yield:

: 898546-99-1
(S)-4-benzyl-3-((2R,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-3-hydroxy-2-methylpropanoyl)oxazolidin-2-one

: 1296147-83-5
5-((2R,3R,4S,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyltetrahydrofuran-2-yl)benzo[d][1,3]dioxole

Guidance literature:: Multi-step reaction with 13 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.08 h

2.1: lithium borohydride / tetrahydrofuran; methanol; diethyl ether / 1 h / 0 - 20 °C

3.1: dipyridinium dichromate / dichloromethane / 12 h / 20 °C / Molecular sieve

4.1: tetrahydrofuran / 0.5 h / 20 °C

5.1: dipyridinium dichromate / dichloromethane / 1.5 h / 20 °C / Molecular sieve

6.1: tetrahydrofuran / 0.75 h / -40 - 20 °C

7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 21 h / 0 - 20 °C

7.2: 1 h

8.1: dipyridinium dichromate / N,N-dimethyl-formamide / 2 h / 20 °C

9.1: cerium(III) chloride / tetrahydrofuran / 0 °C

9.2: -78 - 20 °C

10.1: pyridine; Dess-Martin periodane / dichloromethane / 1 h / 20 °C

11.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 20 °C

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C

13.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 12 h

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; dipyridinium dichromate; lithium borohydride; cerium(III) chloride; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; Dess-Martin periodane; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 4.1: |Grignard Reaction;
DOI:10.1021/acs.joc.5b00945