(R)-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate

Base Information

Chemical Name:(R)-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate
CAS No.:1262487-77-3
Molecular Formula:C₂₃H₂₄O₆
Molecular Weight:396.44
Hs Code.:

Synonyms:(R)-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (R)-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate

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Technology Process of (R)-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate

There total 10 articles about (R)-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate 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: 62.0%

: 621-82-9
Cinnamic acid

: 18439-34-4
(3aR,5R,6S,6aR)-5-((S)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol

: 1262487-77-3
(R)-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate

Guidance literature:: Cinnamic acid; (3aR,5R,6S,6aR)-5-((S)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol; With triphenylphosphine; In tetrahydrofuran; for 0.333333h;

With di-isopropyl azodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; for 5h;
DOI:10.1016/j.tetasy.2010.10.016

Reference yield: 12.0%

: 102-92-1,17082-09-6
Cinnamoyl chloride

: 18439-35-5
(3aR,5R,6S,6aR)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol

: 1262487-77-3
(R)-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate

: 1262487-78-4
(R)-((3aR,5R,6S,6aR)-6-(cinnamoyloxy)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate

Guidance literature:: In 1,2-dichloro-ethane; at 70 ℃; for 20h;
DOI:10.1016/j.tet.2015.05.040

Reference yield:

: 70057-97-5
6-hydroxy-2,2-dimethyl-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

: 1262487-77-3
(R)-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate

: 1262487-78-4
(R)-((3aR,5R,6S,6aR)-6-(cinnamoyloxy)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate

Guidance literature:: Multi-step reaction with 2 steps

1: N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; toluene / 76 h / 0 - 20 °C / Inert atmosphere

2: 1,2-dichloro-ethane / 20 h / 70 °C

With N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; 1,2-dichloro-ethane; toluene; 1: |Grignard Reaction;
DOI:10.1016/j.tet.2015.05.040