Synthesis of 2-spirocyclopropylglucose via condensation of erythrose with the lithium enolate of 2,6-di-tert=butyl-4-methylphenyl cyclopropanecarboxylate

Petter, Russell C.; Kumaravel, Gnanasambandam; Powers, David G.; Chang, C.‐T.

doi:10.1016/s0040-4039(00)79465-2

Cited by 14 publications

(1 citation statement)

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“…One of these methodologies involves the transformation of natural sugars or their derivatives 4a−4e. Another approach consists of the stepwise assembly of the sugar moiety using an aldol condensation of a sterically congested cyclopropanecarboxylic acid ester 4f. An attractive synthetic procedure for the preparation of carbohydrate derivatives — an inverse‐electron‐demand hetero‐Diels−Alder reaction of enol ethers with α,β‐unsaturated carbonyl compounds — has been known for more than 50 years5 and has been used many times for the synthesis of both racemic and enantiopure sugars and their derivatives 6.…”

Section: Introductionmentioning

confidence: 99%

De Novo Synthesis of Racemic Spirocyclopropane‐Annelated 2‐Deoxyhexose Derivatives

et al. 2003

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High‐pressure‐induced inverse‐electron‐demand hetero‐Diels−Alder reactions of ethyl trans‐4‐ethoxy‐2‐oxo‐3‐butenoate (2a) and methyl trans‐4‐benzyloxy‐2‐oxo‐3‐butenoate (2b) with benzyl (cyclopropylidenemethyl) ether (1) each yielded mixtures of two separable diastereomeric esters 7a (64%) and 7b (80%) which, in three subsequent steps, led to the 3‐ethylated and 3‐benzylated α‐ and β‐anomeric benzyl spiro[2‐deoxy‐(D,L)‐arabino‐hexopyranoside‐2,1′‐cyclopropanes] α‐10a,b and β‐10a,b, respectively. The relative configuration of β‐10a was proved by an X‐ray crystal structure analysis. Deprotection of β‐10b was achieved by Pd‐catalyzed hydrogenation in dimethylacetamide leading to spiro[2‐deoxy‐α/β‐2‐(D,L)‐arabino‐hexopyranoside‐2,1′‐cyclopropane] (4). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: Introductionmentioning

confidence: 99%

De Novo Synthesis of Racemic Spirocyclopropane‐Annelated 2‐Deoxyhexose Derivatives

et al. 2003

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Organometallic Derivatives of Cyclopropanes and their Reactions

Goldschmidt

2009

Patai's Chemistry of Functional Groups

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Introduction Metal Derivatives of Cyclopropane Cyclopropylidene Complexes Metal Derivatives of Cyclopropene η 3 ‐Cyclopropenyl Complexes (Metallatetrahedranes) Cyclopropenylidene Complexes Metal Derivatives of Methylenecyclopropane Methylenecyclopropene Complexes (Triafulvenes) Acknowledgments

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ChemInform Abstract: Synthesis of 2‐Spirocyclopropylglucose via Condensation of Erythrose with the Lithium Enolate of 2,6‐Di‐tert‐butyl‐4‐methylphenyl Cyclopropanecarboxylate.

et al. 1991

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Synthesis of 2-spirocyclopropylglucose via condensation of erythrose with the lithium enolate of 2,6-di-tert=butyl-4-methylphenyl cyclopropanecarboxylate

Cited by 14 publications

References 25 publications

De Novo Synthesis of Racemic Spirocyclopropane‐Annelated 2‐Deoxyhexose Derivatives

De Novo Synthesis of Racemic Spirocyclopropane‐Annelated 2‐Deoxyhexose Derivatives

Organometallic Derivatives of Cyclopropanes and their Reactions

ChemInform Abstract: Synthesis of 2‐Spirocyclopropylglucose via Condensation of Erythrose with the Lithium Enolate of 2,6‐Di‐tert‐butyl‐4‐methylphenyl Cyclopropanecarboxylate.

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