Dihydroxylation of 4-substituted 1,2-dioxines: a concise route to branched erythro sugars

Research output: Contribution to journalJournal article

Standard

Dihydroxylation of 4-substituted 1,2-dioxines : a concise route to branched erythro sugars. / Robinson, Tony V; Pedersen, Daniel Sejer; Taylor, Dennis K; Tiekink, Edward R T.

In: Journal of Organic Chemistry, Vol. 74, No. 14, 2009, p. 5093-5096.

Research output: Contribution to journalJournal article

Harvard

Robinson, TV, Pedersen, DS, Taylor, DK & Tiekink, ERT 2009, 'Dihydroxylation of 4-substituted 1,2-dioxines: a concise route to branched erythro sugars', Journal of Organic Chemistry, vol. 74, no. 14, pp. 5093-5096. https://doi.org/10.1021/jo900669u

APA

Robinson, T. V., Pedersen, D. S., Taylor, D. K., & Tiekink, E. R. T. (2009). Dihydroxylation of 4-substituted 1,2-dioxines: a concise route to branched erythro sugars. Journal of Organic Chemistry, 74(14), 5093-5096. https://doi.org/10.1021/jo900669u

Vancouver

Robinson TV, Pedersen DS, Taylor DK, Tiekink ERT. Dihydroxylation of 4-substituted 1,2-dioxines: a concise route to branched erythro sugars. Journal of Organic Chemistry. 2009;74(14):5093-5096. https://doi.org/10.1021/jo900669u

Author

Robinson, Tony V ; Pedersen, Daniel Sejer ; Taylor, Dennis K ; Tiekink, Edward R T. / Dihydroxylation of 4-substituted 1,2-dioxines : a concise route to branched erythro sugars. In: Journal of Organic Chemistry. 2009 ; Vol. 74, No. 14. pp. 5093-5096.

Bibtex

@article{8a0c25107cff11de8bc9000ea68e967b,
title = "Dihydroxylation of 4-substituted 1,2-dioxines: a concise route to branched erythro sugars",
abstract = "The synthesis of 2-C-branched erythritol derivatives, including the plant sugar (+/-)-2-C-methylerythritol 2, was achieved through a dihydroxylation/reduction sequence on a series of 4-substituted 1,2-dioxines 3. The asymmetric dihydroxylation of 1,2-dioxines was examined, providing access to optically enriched dihydroxy 1,2-dioxanes 4. The synthesized 1,2-dioxanes were converted to other erythro sugar analogues and tetrahydrofurans through controlled cleavage of the endoperoxide linkage.",
keywords = "Former Faculty of Pharmaceutical Sciences",
author = "Robinson, {Tony V} and Pedersen, {Daniel Sejer} and Taylor, {Dennis K} and Tiekink, {Edward R T}",
year = "2009",
doi = "10.1021/jo900669u",
language = "English",
volume = "74",
pages = "5093--5096",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "14",

}

RIS

TY - JOUR

T1 - Dihydroxylation of 4-substituted 1,2-dioxines

T2 - a concise route to branched erythro sugars

AU - Robinson, Tony V

AU - Pedersen, Daniel Sejer

AU - Taylor, Dennis K

AU - Tiekink, Edward R T

PY - 2009

Y1 - 2009

N2 - The synthesis of 2-C-branched erythritol derivatives, including the plant sugar (+/-)-2-C-methylerythritol 2, was achieved through a dihydroxylation/reduction sequence on a series of 4-substituted 1,2-dioxines 3. The asymmetric dihydroxylation of 1,2-dioxines was examined, providing access to optically enriched dihydroxy 1,2-dioxanes 4. The synthesized 1,2-dioxanes were converted to other erythro sugar analogues and tetrahydrofurans through controlled cleavage of the endoperoxide linkage.

AB - The synthesis of 2-C-branched erythritol derivatives, including the plant sugar (+/-)-2-C-methylerythritol 2, was achieved through a dihydroxylation/reduction sequence on a series of 4-substituted 1,2-dioxines 3. The asymmetric dihydroxylation of 1,2-dioxines was examined, providing access to optically enriched dihydroxy 1,2-dioxanes 4. The synthesized 1,2-dioxanes were converted to other erythro sugar analogues and tetrahydrofurans through controlled cleavage of the endoperoxide linkage.

KW - Former Faculty of Pharmaceutical Sciences

U2 - 10.1021/jo900669u

DO - 10.1021/jo900669u

M3 - Journal article

C2 - 19588997

VL - 74

SP - 5093

EP - 5096

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 14

ER -

ID: 13435608