(3aR,4R,7S,8aR)-Tetrahydro-7-hydroxy-2,2-dimethyl-4,7-methano-1,3-dioxolo[4,5-c]oxepin-6(4H)-one synthesis

9synthesis methods

Product Name:(3aR,4R,7S,8aR)-Tetrahydro-7-hydroxy-2,2-dimethyl-4,7-methano-1,3-dioxolo[4,5-c]oxepin-6(4H)-one
CAS Number:32384-42-2
Molecular formula:C10H14O5
Molecular Weight:214.22

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(3aR,4R,7S,8aR)-Tetrahydro-7-hydroxy-2,2-dimethyl-4,7-methano-1,3-dioxolo[4,5-c]oxepin-6(4H)-one

32384-42-2
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Yield: 98%

Reaction Conditions:

with toluene-4-sulfonic acid in acetone for 1 h;Reflux;

Steps:

4.2.1. (3aR,7R,7aS)-7-Hydroxy-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one (12)
A suspension of D-(-)-quinic acid (8) (1.52 g,7.89 mmol), 2,2-dimethoxypropane (3.50 mL, 28.6 mmol), and p-TsOH*H2O (151.7 mg, 0.80 mmol) in acetone (78 mL) was stirred for 1 h under reflux, and Et3N (0.3 mL, 2.2 mmol) was added to the mixture. The resulting mixture was concentrated and the residual oil was purified by chromatography on silica gel (hexane/EtOAc) to afford the corresponding lactone (1.64 g, 98%) as solids.

References:

Kawashima, Hidehisa;Sakai, Masahiro;Kaneko, Yuki;Kobayashi, Yuichi [Tetrahedron,2015,vol. 71,# 16,art. no. 26481,p. 2387 - 2392]

77-95-2
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