Reaction of Cyclic Sulfates with Phosphines

Kim, Kwan Soo; Joo, Yung Hyup; Kim, In Wook; Lee, Kyoung Rim; Cho, Duk Young; Kim, Minjeong; Cho, In Haeng

doi:10.1080/00397919408011712

Cited by 14 publications

(2 citation statements)

References 6 publications

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“…Similarly, reaction with potassium selenocyanate followed by treatment with sodium borohydride led to olefins also in one pot (see Figure ). Simultaneously to our studies, cyclic sulfates of vic- diols have also been transformed into olefins by treatment with phosphine or by telluride ion generated in situ by reduction of elemental Te 1 t …”

Section: Introductionsupporting

confidence: 55%

Applications of Cyclic Sulfates ofvic-Diols: Synthesis of Episulfides, Olefins, and Thio Sugars

et al. 1997

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A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic polyols derived from chiral glycerine, 1,2-isopropylidenehexofuranoses with different subtituents at C-3, and dimethyl acetals derived from pentoses and hexoses. The methodology is highly versatile, and its applicability has been demonstrated by the synthesis of different 4- and 5-thiosugars by opening of the thiirane ring with sodium acetate or lithium aluminum hydride. Reduction with lithium aluminum hydride of the thiocyanate sulfate potassium salt obtained by the opening of cyclic sulfate with KSCN allowed the direct synthesis of 5-deoxy-4-thio- and 6-deoxy-5-thiosugars. Cyclic thiosugars with the sulfur atom in the ring are obtained by acidic hydrolysis of the 5-thiol derivatives of 1,2-O-isopropylidenehexofuranoses and 4-thiopentose dimethyl acetals. Using this method, an efficient synthesis of 5-thio-l-fucose as well as the synthesis of 2,5-dideoxy-4-thiofuranose is described.

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Section: Introductionsupporting

confidence: 55%

Applications of Cyclic Sulfates ofvic-Diols: Synthesis of Episulfides, Olefins, and Thio Sugars

et al. 1997

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“…Olefins can be obtained directly from vicinal diols by treatment with titanium metal [41,42], Me 3 SiCl-NaI [43], Ph 3 P-I 2 -imidazole [44], Ph 2 PCl-I 2 -imidazole [45], PBr 3 -CuBr-Zn [46] or tungsten reagent such as K 2 WCl 6 [47]. However the main methods require the introduction of activating groups: (i) vicinal bromoacetate [48]; (ii) cyclic thionocarbonate [49,50]; (iii) 1,3-dioxolane [51][52][53][54]; (iv) vicinal dixanthates [55][56][57][58]; (v) vicinal disulfates [59,60]; (vi) cyclic phosphates [61][62][63]; (vii) phosphoramidate [61][62][63]; (viii) cyclic sulfate [64][65][66][67][68]. Few of the known methods for conversion of vicinal diols to olefins have been applied to ribonucleosides.…”

Section: Garreg-samuelsson Eliminationmentioning

confidence: 99%

Synthesis of 2,3-Didehydro-2,3-dideoxynucleosides via Nucleoside Route.

Len¹,

Postel²

2006

COS

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2',3'-Didehydro-and 2',3'-dideoxynucleosides are both potent antiviral agents. In particular, they are Nucleoside Reverse Transcriptase Inhibitors and hence active against HIV, the ethiological agent of AIDS. They are also intermediates for the synthesis of antiviral 2',3'-dideoxynucleosides. Various aspects of synthetic routes to 2',3'-unsaturated nucleosides are reviewed with examples being chosen from work published between 1966 and 2003.

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1,3,2-Dioxathiolane 2,2-Dioxide

Lynch

2009

Encyclopedia of Reagents for Organic Synthesis

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Reaction of Cyclic Sulfates with Phosphines

Cited by 14 publications

References 6 publications

Applications of Cyclic Sulfates ofvic-Diols: Synthesis of Episulfides, Olefins, and Thio Sugars

Applications of Cyclic Sulfates ofvic-Diols: Synthesis of Episulfides, Olefins, and Thio Sugars

Synthesis of 2,3-Didehydro-2,3-dideoxynucleosides via Nucleoside Route.

1,3,2-Dioxathiolane 2,2-Dioxide

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