Syntheses of four D- and L-hoxoses via diastereoselective and enantioselective dihydroxylation reactions

Joel M. Harris; Mark D. Keränen; Hang Nguyen; Victor G. Young; George A. O’Doherty

doi:10.1016/S0008-6215(00)00031-8

Syntheses of four D- and L-hoxoses via diastereoselective and enantioselective dihydroxylation reactions

Joel M. Harris, Mark D. Keränen, Hang Nguyen, Victor G. Young, George A. O’Doherty

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

113 Scopus citations

Abstract

An expeditious approach to various protected hexoses has been developed by the use of the Sharpless catalytic asymmetric dihydroxylation reaction. Applying the Sharpless catalytic asymmetric dihydroxylation reaction on vinylfuran, diols with high enantioexcess are produced. The resulting diols can be stereoselectively transformed into either protected D- or L-mannose in five steps and approximately 39% yield from furfural. Similarly, both D- and L-talose and gulose have been synthesized in 19% overall yields, respectively. Using a modified strategy, both protected D- and L-gulo- and allo-sugar-δ-lactones were synthesized in eight steps and ~-20% overall yield from furfural.

Original language	English (US)
Pages (from-to)	17-36
Number of pages	20
Journal	Carbohydrate Research
Volume	328
Issue number	1
DOIs	https://doi.org/10.1016/S0008-6215(00)00031-8
State	Published - Aug 16 2000

Bibliographical note

Funding Information:
We thank the University of Minnesota (Grant-in-Aid program), the ACS for an Institutional Research Grant (IRG-58-001-40-IRG-19), the American Chemical Society–Petroleum Research Fund (ACS–PRF#33953-G1) and the Arnald and Mabel Beckman Foundation for their generous support of our program. We would also like to thank Dr Dirk Friedrich (Hoechst Marion Roussel) for his help in the structure determination of 1a and 13 .

Keywords

AD mix
Allose
Dihydroxylation
Enantioselective synthesis
Gulose
Mannose
Sugar lactone
Talose
Vinylfuran

Publisher link

10.1016/S0008-6215(00)00031-8

Find It

Find It at U of M Libraries

Cite this

@article{aa115b5e8b094c99b04877c5ceadc2f4,

title = "Syntheses of four D- and L-hoxoses via diastereoselective and enantioselective dihydroxylation reactions",

abstract = "An expeditious approach to various protected hexoses has been developed by the use of the Sharpless catalytic asymmetric dihydroxylation reaction. Applying the Sharpless catalytic asymmetric dihydroxylation reaction on vinylfuran, diols with high enantioexcess are produced. The resulting diols can be stereoselectively transformed into either protected D- or L-mannose in five steps and approximately 39% yield from furfural. Similarly, both D- and L-talose and gulose have been synthesized in 19% overall yields, respectively. Using a modified strategy, both protected D- and L-gulo- and allo-sugar-δ-lactones were synthesized in eight steps and ~-20% overall yield from furfural.",

keywords = "AD mix, Allose, Dihydroxylation, Enantioselective synthesis, Gulose, Mannose, Sugar lactone, Talose, Vinylfuran",

author = "Harris, {Joel M.} and Ker{\"a}nen, {Mark D.} and Hang Nguyen and Young, {Victor G.} and O{\textquoteright}Doherty, {George A.}",

note = "Funding Information: We thank the University of Minnesota (Grant-in-Aid program), the ACS for an Institutional Research Grant (IRG-58-001-40-IRG-19), the American Chemical Society–Petroleum Research Fund (ACS–PRF#33953-G1) and the Arnald and Mabel Beckman Foundation for their generous support of our program. We would also like to thank Dr Dirk Friedrich (Hoechst Marion Roussel) for his help in the structure determination of 1a and 13 .",

year = "2000",

month = aug,

day = "16",

doi = "10.1016/S0008-6215(00)00031-8",

language = "English (US)",

volume = "328",

pages = "17--36",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier Ltd",

number = "1",

}

TY - JOUR

T1 - Syntheses of four D- and L-hoxoses via diastereoselective and enantioselective dihydroxylation reactions

AU - Harris, Joel M.

AU - Keränen, Mark D.

AU - Nguyen, Hang

AU - Young, Victor G.

AU - O’Doherty, George A.

N1 - Funding Information: We thank the University of Minnesota (Grant-in-Aid program), the ACS for an Institutional Research Grant (IRG-58-001-40-IRG-19), the American Chemical Society–Petroleum Research Fund (ACS–PRF#33953-G1) and the Arnald and Mabel Beckman Foundation for their generous support of our program. We would also like to thank Dr Dirk Friedrich (Hoechst Marion Roussel) for his help in the structure determination of 1a and 13 .

PY - 2000/8/16

Y1 - 2000/8/16

N2 - An expeditious approach to various protected hexoses has been developed by the use of the Sharpless catalytic asymmetric dihydroxylation reaction. Applying the Sharpless catalytic asymmetric dihydroxylation reaction on vinylfuran, diols with high enantioexcess are produced. The resulting diols can be stereoselectively transformed into either protected D- or L-mannose in five steps and approximately 39% yield from furfural. Similarly, both D- and L-talose and gulose have been synthesized in 19% overall yields, respectively. Using a modified strategy, both protected D- and L-gulo- and allo-sugar-δ-lactones were synthesized in eight steps and ~-20% overall yield from furfural.

AB - An expeditious approach to various protected hexoses has been developed by the use of the Sharpless catalytic asymmetric dihydroxylation reaction. Applying the Sharpless catalytic asymmetric dihydroxylation reaction on vinylfuran, diols with high enantioexcess are produced. The resulting diols can be stereoselectively transformed into either protected D- or L-mannose in five steps and approximately 39% yield from furfural. Similarly, both D- and L-talose and gulose have been synthesized in 19% overall yields, respectively. Using a modified strategy, both protected D- and L-gulo- and allo-sugar-δ-lactones were synthesized in eight steps and ~-20% overall yield from furfural.

KW - AD mix

KW - Allose

KW - Dihydroxylation

KW - Enantioselective synthesis

KW - Gulose

KW - Mannose

KW - Sugar lactone

KW - Talose

KW - Vinylfuran

UR - http://www.scopus.com/inward/record.url?scp=0343526339&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0343526339&partnerID=8YFLogxK

U2 - 10.1016/S0008-6215(00)00031-8

DO - 10.1016/S0008-6215(00)00031-8

M3 - Article

C2 - 11005573

AN - SCOPUS:0343526339

SN - 0008-6215

VL - 328

SP - 17

EP - 36

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 1

ER -

Syntheses of four D- and L-hoxoses via diastereoselective and enantioselective dihydroxylation reactions

Abstract

Bibliographical note

Keywords

Publisher link

Find It

Other files and links

Fingerprint

Cite this