Synthesis of carba-β-d- and l-idopyranosides by rearrangement of unsaturated sugars

Sollogoub, Matthieu; Pearce, Alan J.; Herault, Alexandre; Sînaÿ, Pierre

doi:10.1016/s0957-4166(99)00479-6

Cited by 46 publications

(26 citation statements)

References 27 publications

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“…82 Modification at C-5 of a pseudodisaccharide (281) obtained by this method gave a carbaidopyranoside pseudodisaccharide (284) (Scheme 13). 83 C-6-Deprotected carbaidopyranosides have been converted to carbaglucopyranosides by an oxidation-epimerisation-reduction sequence, although this has only been shown on a glycosidically linked pseudodisaccharide (285?286) as yet (Scheme 14). 84 Treatment of the exo-glycal rearrangement precursors with trimethylaluminium instead of TIBAL gave a rearrangement to cyclohexane products with no debenzylation observed.…”

Section: Other Methods For Ether-linked Carbadisaccharide Synthesismentioning

confidence: 99%

Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides

Cumpstey

2009

Carbohydrate Research

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Section: Other Methods For Ether-linked Carbadisaccharide Synthesismentioning

confidence: 99%

Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides

Cumpstey

2009

Carbohydrate Research

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“…112 For example Cfuryl glycoside, derived from D-glucose (155c þ 229), was converted to a partially protected carba-a-D-idopyranoside 230 (Scheme 52). 113 The furyl group was used as a masked form of the hydroxymethyl moiety at C-5.…”

Section: Rearrangement Of Cyclic Sugarsmentioning

confidence: 99%

An overview of key routes for the transformation of sugars into carbasugars and related compounds

Soengas¹,

Otero²,

Rauter³

et al. 2012

Carbohydrate Chemistry

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“…When the aglycon moiety was activated by electrondonating groups, it appeared that the increased electrondonating ability was along with higher yield, shorter reaction time, and fewer open-chain byproducts [48,49,50] (Scheme 22, Scheme 23).…”

Section: Ferrier II Rearrangement Promoted By Aluminium Saltsmentioning

confidence: 99%

From Exocyclic-Olefinic Carbohydrate Derivatives to Functionalized Carbocyclic Compounds

Zhou¹,

Wang²,

Zhang³

et al. 2006

COC

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As the structural constituents of many naturally occurring molecules, synthesis of functionalized carbocyclic derivatives has been widely investigated. Among numerous approaches to construct carbocyclic compounds, there is an efficient way of forming carbocyclic derivatives by the use of various monosaccharides as chiral building blocks. In this review, synthetic conversions to functionalized carbocyclic compounds from exocyclic-olefinic saccharides and their applications to synthesis of some natural products or natural product-like analogues will be discussed. The emphases will be put on the latest methodology developments of ring-conversion rearrangement reactions catalyzed by metal catalysts.

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Synthesis of carba-β-d- and l-idopyranosides by rearrangement of unsaturated sugars

Cited by 46 publications

References 27 publications

Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides

Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides

An overview of key routes for the transformation of sugars into carbasugars and related compounds

From Exocyclic-Olefinic Carbohydrate Derivatives to Functionalized Carbocyclic Compounds

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