Synthetic studies of carbohydrate derivatives with the photochemical reaction I. Photochemical addition of thioacetic acid, benzyl mercaptan and 1,3-dioxolane.

Matsuura, Kazuo; Maeda, S.; Araki, Younosuke; Ishido, Yoshiharu; Murai, T.

doi:10.1016/s0040-4039(01)98361-3

Cited by 13 publications

(2 citation statements)

References 5 publications

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“…Its utility in the synthesis of branched-chain sugars has been explored by Jewel and Szarek (7) and Matsuura and co-workers (8). However, with these simple olefins, the additions are usually neither regionor stereoselective.…”

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confidence: 99%

Synthetic applications of the photochemically induced addition of oxycarbinyl species to α-enones. Part II. The addition of ketals, aldehydes, and polyfunctional species

Fraser‐Reid¹,

Anderson²,

Hicks³

et al. 1977

Can. J. Chem.

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Alcohols possessing an α-hydrogen, acetals, and aldehydes undergo photochemically induced conjugate addition to a variety of α-enones to give 1,4-ketols, 1,4-keto ketols and 1,4-diketones respectively. It appears that the aldehydes frequently succeed where acetals and alcohols fail, and acetals where alcohols fail. It is therefore possible to employ polyfunctional addenda and achieve addition at only one of the activated sites. The reactions are always regiospecific and are frequently completely stereoselective.

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mentioning

confidence: 99%

Synthetic applications of the photochemically induced addition of oxycarbinyl species to α-enones. Part II. The addition of ketals, aldehydes, and polyfunctional species

Fraser‐Reid¹,

Anderson²,

Hicks³

et al. 1977

Can. J. Chem.

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“…Deoxy sugars have also been prepared by photodecomposition of dimethyl thiocarbamate derivatives(102). Sulfur-containing sugars have been prepared by the photo-addition of mercaptans to unsaturated sugars(103)(104).. The relatively high efficiency with which sulfur compounds ab sorb light(105,106), especially compounds which contain the thiocarbonyl group, has resulted in a large number of reports on the photo chemistry of organic sulfur compounds(105,107,108).…”

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confidence: 99%

Photolysis of some carbohydrate dithiobis(thioformates)

Stout¹,

Doane²,

Russell³

et al. 1975

J. Org. Chem.

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The photolysis of several oxidatively coupled xanthates of model sugar compounds has been investigated. The photolysis of bis (1,2: 3,4-di-Oj-isopropylidene-Q'-'D-galactopyranos-G-yl) dithiobis-(thioformate) (XXXIII) gave the xanthate ester, bis(6-deoxy-l,2:3,4di-Oj-isopropylidene-^-D-galactopyranos-6-y 1) 6-jO, 6 f-^Sj-dithiocarbonate (LXX) in 78% yield. In concentrated solutions, bis(1,2:3,4-di-0isopropylidene-^j-D-galactopyranos-6-y1) tetrathiobis (thioformate) (LXIX) was produced along with LXX. The photolysis of bis (1,2:5,6di-0_-isopropylidene-G^-D-glucofurano.s-3-yl) dithiobis (thioformate) (XIV) gave bis(3-deoxy-l,2:5,6-di-0^isopropylidene-a^-D-glucofuranos-3-yl) 3-jO, 3 8-Sr-dithiocarbonate (LXXVl), in which an oxygen atom on the sugar ring has been replaced with sulfur with retention of configuration. A cyclic mechanism in which either the excited thiocarbonyl sulfur or a sulfur of the disulfide linkage attacks the carbon giving a front side displacement of oxygen has been proposed to account for the observed results.

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ChemInform Abstract: PHOTOCHEMISCHE RK. BEI KOHLENHYDRATEN 1. MITT. PHOTOCHEMISCHE ADDITION VON THIOESSIGSAEURE, BENZYLMERCAPTAN UND 1,3‐DOXOLAN

Matsuura¹,

Maeda²,

Araki³

et al. 1970

Chemischer Informationsdienst. Organische Chemie

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Synthetic studies of carbohydrate derivatives with the photochemical reaction I. Photochemical addition of thioacetic acid, benzyl mercaptan and 1,3-dioxolane.

Cited by 13 publications

References 5 publications

Synthetic applications of the photochemically induced addition of oxycarbinyl species to α-enones. Part II. The addition of ketals, aldehydes, and polyfunctional species

Synthetic applications of the photochemically induced addition of oxycarbinyl species to α-enones. Part II. The addition of ketals, aldehydes, and polyfunctional species

Photolysis of some carbohydrate dithiobis(thioformates)

ChemInform Abstract: PHOTOCHEMISCHE RK. BEI KOHLENHYDRATEN 1. MITT. PHOTOCHEMISCHE ADDITION VON THIOESSIGSAEURE, BENZYLMERCAPTAN UND 1,3‐DOXOLAN

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