(1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl cinnamate

Base Information

• Chemical Name: (1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl cinnamate
• CAS No.: 1262487-74-0
• Molecular Formula: C₂₂H₂₂O₅
• Molecular Weight: 366.414

Synonyms:(1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl cinnamate

Chemical Property of (1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl cinnamate

Chemical Property:

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Technology Process of (1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl cinnamate

There total 1 articles about (1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl 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: 70.0%

(4S,5R,6R,7R,E)-ethyl 5-(allyloxy)-7-cinnamoyloxy-4,6-dihydroxy-7-phenylhept-2-enoate (1262487-73-9) → (1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl cinnamate (1262487-74-0)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; for 12h; Reflux;

DOI:10.1016/j.tetasy.2010.10.016

Reference yield: 82.0%

(1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl cinnamate (1262487-74-0) + 2,2-dimethoxy-propane (77-76-9) → (R)-((4R,4aR,8aS)-2,2-dimethyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-4-yl)(phenyl)methyl cinnamate (1262487-75-1)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.tetasy.2010.10.016

Reference yield: 73.0%

(1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl cinnamate (1262487-74-0) + Cinnamic acid (621-82-9) → (2E,2'E)-((1R,2R)-1-((2R,3S)-3-(cinnamoyloxy)-3,6-dihydro-2H-pyran-2-yl)-2-phenylethane-1,2-diyl) bis(3-phenylacrylate) (1262487-71-7)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.tetasy.2010.10.016

upstream raw materials:

(4S,5R,6R,7R,E)-ethyl 5-(allyloxy)-7-cinnamoyloxy-4,6-dihydroxy-7-phenylhept-2-enoate

Downstream raw materials:

(2E,2'E)-((1R,2R)-1-((2R,3S)-3-(cinnamoyloxy)-3,6-dihydro-2H-pyran-2-yl)-2-phenylethane-1,2-diyl) bis(3-phenylacrylate)

(R)-((4R,4aR,8aS)-2,2-dimethyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-4-yl)(phenyl)methyl cinnamate

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