Synthesis of l -2-spirocyclopropyl-2-deoxyarabinose

Petter, Russell C.; Powers, David G.

doi:10.1016/s0040-4039(01)80275-6

Cited by 25 publications

(11 citation statements)

References 31 publications

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“…H); 4.91 (d, J = 10. 9,4.62(d,J= 10.7,PhCH);4.56(d,J= 12.3,PhCH);4.55(d,J=11.5,PhCH);3.91(d,J=9.1,H-C(8);irrad.at 1.60: NOE (weak)); 3.86 (1. J = 9.4, H-C(6)); 3.73 (m, 2 CH-C(5)); 3.67 ( I , J = 9.1, H-C (7); irrad.…”

Section: -Tris(henzyloxy)-s-[ (Benzyloxy)meth~~l]-4-oxaspiro[25]octamentioning

confidence: 99%

Glycosylidene Carbenes. Part 3. Synthesis of Spirocyclopropanes

Vasella¹,

Waldraff²

1991

Helvetica Chimica Acta

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Thermolysis of the glycosylidene-derived 0 -benzylated diazirine 1 in the presence of N-phenylmaleimide (2), acrylonitrile (3), dimethyl fumarate (4), or dimethyl maleate (5) led in good yields to mixtures of the spirocyclopropanes 6/7, S l l , 12/13, and 12/13/16/17. The diastereoselectivity depends upon the alkene. The cycloaddition of 1 to 5 is not diastereospecific, in keeping with previous results. Deprotection of 12, 13, 16, and 17 yielded the tetrols 14, 15, 18, and 19, respectively.

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Section: -Tris(henzyloxy)-s-[ (Benzyloxy)meth~~l]-4-oxaspiro[25]octamentioning

confidence: 99%

Glycosylidene Carbenes. Part 3. Synthesis of Spirocyclopropanes

Vasella¹,

Waldraff²

1991

Helvetica Chimica Acta

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“…To the best of our knowledge, only a few syntheses of spirocyclopropane‐annelated sugars or sugar derivatives have been developed 4. 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.…”

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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“…tributyltin hydride and azobis(isobutyronitrile) in xylene at 140°C, however, affords the totally dehalogenated cyclopropane 144 in 64% yield. Hydrolytic deprotection of 144 by aqueous acetic acid affords 145 as a 10.6:2.9:1.0 mixture of pyranose/furanose/open chain, as determined by NMR spectroscopy 47. …”

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confidence: 97%

Preparation and Structure Classification of Heteraspiro[m.n]alkanes

Undheim¹

2014

Synthesis

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The fundamental spirane framework consists of two monocyclic rings linked in an orthogonal relationship by a common ring atom. In spiranes with no annular heteroatom, four carbon atoms are bonded directly to the quaternary spirocarbon. The spirocarbon may be the site of a stereogenic centre and stereoisomerism. This review covers families of spiranes where one or both rings carry additional annular heteroatoms, mainly N, O or S. The heteroatoms are indicated by replacement prefixes. In general, the term 'hetera' denotes a nonspecified annulated heteroatom which may be N, O, or S. The presentation is arranged with preference for the size of the monocyclic rings and thereafter the nature of the annular heteroatoms.In general, rigid spirocyclic structures provide wide variations of spatial disposition of the functional groups. When the spirane skeleton consists of small-or medium-sized rings, a rigid structure results that also confers stiffness onto molecules in which the spirane may be embedded. The rigidity of such systems provides a stiff framework for the attachment of pharmacophoric groups, or a rigid framework for metal coordination. Reference is made to a limited number of studies of physico-chemical properties of small-ring systems. Nitrogen-containing systems are most common. 1 Introduction and Definitions 2 Heteraspiro[2.m]alkanes 3 Heteraspiro[3.m]alkanes 4 Heteraspiro[4.m]alkanes 5 Heteraspiro[5.m]alkanes

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Synthesis of l -2-spirocyclopropyl-2-deoxyarabinose

Cited by 25 publications

References 31 publications

Glycosylidene Carbenes. Part 3. Synthesis of Spirocyclopropanes

Glycosylidene Carbenes. Part 3. Synthesis of Spirocyclopropanes

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

Preparation and Structure Classification of Heteraspiro[m.n]alkanes

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