(2R,4aR,6S,6aS,7S,9R,9aR,9bS)-9a-Formyl-6-methoxy-2-phenyl-9-propionyl-octahydro-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxine-7-carboxylic acid

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Chemical Name:(2R,4aR,6S,6aS,7S,9R,9aR,9bS)-9a-Formyl-6-methoxy-2-phenyl-9-propionyl-octahydro-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxine-7-carboxylic acid
CAS No.:910324-24-2
Molecular Formula:C₂₂H₂₆O₈
Molecular Weight:418.444
Hs Code.:

Synonyms:(2R,4aR,6S,6aS,7S,9R,9aR,9bS)-9a-Formyl-6-methoxy-2-phenyl-9-propionyl-octahydro-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxine-7-carboxylic acid

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Chemical Property of (2R,4aR,6S,6aS,7S,9R,9aR,9bS)-9a-Formyl-6-methoxy-2-phenyl-9-propionyl-octahydro-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxine-7-carboxylic acid

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Technology Process of (2R,4aR,6S,6aS,7S,9R,9aR,9bS)-9a-Formyl-6-methoxy-2-phenyl-9-propionyl-octahydro-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxine-7-carboxylic acid

There total 2 articles about (2R,4aR,6S,6aS,7S,9R,9aR,9bS)-9a-Formyl-6-methoxy-2-phenyl-9-propionyl-octahydro-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxine-7-carboxylic acid 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:

: 676451-02-8
(1S,2S,4R,7R,9S,10S,11S,13R)-1,13-dicarbaldehyde-9-methoxy-4-phenyl-3,5,8-trioxatricyclo[8.3.0^1,10.0^2.7]tridecane-11-carboxylic acid methyl ester

: 925-90-6
ethylmagnesium bromide

: 910324-24-2
(2R,4aR,6S,6aS,7S,9R,9aR,9bS)-9a-Formyl-6-methoxy-2-phenyl-9-propionyl-octahydro-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxine-7-carboxylic acid

Guidance literature:: (1S,2S,4R,7R,9S,10S,11S,13R)-1,13-dicarbaldehyde-9-methoxy-4-phenyl-3,5,8-trioxatricyclo[8.3.0^1,10.0^2.7]tridecane-11-carboxylic acid methyl ester; ethylmagnesium bromide; In tetrahydrofuran; at -30 ℃; for 0.833333h;

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 12h;

With jones reagent; In acetone; at 0 ℃; for 0.25h;
DOI:10.1021/ol061390i

Reference yield:

: 193271-77-1
(1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carbaldehyde

: 910324-24-2
(2R,4aR,6S,6aS,7S,9R,9aR,9bS)-9a-Formyl-6-methoxy-2-phenyl-9-propionyl-octahydro-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxine-7-carboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: O₃; NaHCO₃ / CH₂Cl₂ / -78 °C

1.2: 92.3 percent / Ac₂O; Et₃N / CH₂Cl₂ / 1 h / 20 °C

2.1: tetrahydrofuran / 0.83 h / -30 °C

2.2: aq. LiOH / tetrahydrofuran / 12 h / 20 °C

2.3: Jones reagent / acetone / 0.25 h / 0 °C

With sodium hydrogencarbonate; ozone; In tetrahydrofuran; dichloromethane; 2.3: Jones oxidation;
DOI:10.1021/ol061390i