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Synthetic Studies of Carbohydrate Derivatives by Photochemical Reactions. Part 16. Synthesis of DL-Apiose Derivatives by Photochemical Cycloaddition of 1,3-Dihydroxypropan-2-one Derivatives with Ethenediol or Ethenol Derivatives

DOI: 10.1039/P19810000012

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 12 - 23 (1981)

Update date:2022-07-30

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Authors:

Araki, YounosukeAraki, Younosuke

Nagasawa, Jun-ichiNagasawa, Jun-ichi

Ishido, YoshiharuIshido, Yoshiharu

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Article abstract of DOI:10.1039/P19810000012

Irradiation of a benzene solution of 1,3-diacetoxypropan-2-one (5) and 1,3-dioxol-2-one (6) with a high-pressure mercury lamp gave a photocycloaddition product, (7-acetoxymethyl-3-oxo-2,4,6-trioxabicyclo<3.2.0>heptan-7-yl)-methyl acetat (7) (55percent yield).Similar photocycloadditions of (5)with (Z)-vinylene diacetate (23), with (Z)-2-(benzyloxy)vinyl acetate (25), with 2,3-dihydro-1,4-dioxin (27), with vinyl acetate (28), with isopropenyl acetate (29), with ethoxyethene (30), and with 1,1-diethoxyethene (43) afforded cis-4,4-bis(acetoxymethyl)oxetan-2,3-diyl diacetat (31) (46percent yield) and the trans-isomer (32) (49percent yield); 2,2-bis(acetoxymethyl)-4-(benzyloxy)-oxetan-3-yl acetate (33) (composed of the two isomers; 11percent and 26percent yields) and 4,4-bis(acetoxymethyl)-3-benzyloxy)oxetan-2-yl acetate (38) (composed of the two isomers; 11percent and 9percent yields); (8-acetoxymethyl-2,5,7-trioxabicyclo<4.2.0>oct-8-yl)methyl acetate (34) (25percent yield); 2,2-bis(acetoxymethyl)oxetan-3-yl acetate (35) (28percent yield) and 4,4-bis(acetoxymethyl)oxetan-2-yl acetate (39) (15percent yield); 2,2-bis(acetoxymethyl)-3-methyloxetan-3-yl acetate (36) (55percent yield); (2-acetoxymethyl-3-ethoxyoxetan-2-yl)methyl acetate (37) (53percent yield); and (2-acetoxymethyl-3,3-diethoxyoxetan-2-yl)methyl acetate (44) (48percent yield) and ethyl 4-acetoxy-3-acetoxymethyl-3-hydroxybutyrate (45) (19percent yield), respectively.The reaction of (5) with (43) was also induced thermally togive ethyl 4-acetoxy-3-(acetoxymethyl)coronate (46) (24percent yield) in addition to (45) (20percent yield).Photocycloaddition of diethyl mesoxalate (21) with (6) gave diethyl 3-oxo-2,4,6-trioxabicyclo<3.2.0>heptane-7,7-dicarboxylate (22) (23percent yield).On the other hand, the reactions of 1,3-dimethoxy- (8) and 1,3-bis(benzyloxy)-propan-2-one (13) respectively with (6) afforded none of the expected photocycloadducts, but several products due to the intramolecular hydrogen abstraction from (8) and (13).The reaction of 2,2-dimethyl-1,3-dioxan-5-one (2) with (6) was also accompanied by predominant decomposition of (20).

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