Cyclopentane cyclitols

Other compounds which will receive attention here include the 1,2-an-hydroinositols, which serve as extremely versatile, synthetic intermediates the first cyclopentane cyclitols and a pseudo-hexose (an aldohexo-pyranose having the ring-oxygen atom replaced by a methylene group). 

The cyclopentane cyclitols have been characterized by nuclear magnetic resonance. The conformational analysis of cyclopentene and of poly-substituted cyclopentanes has been discussed. 

A crystal structural analysis of mwco-inositol is referred to in Chapter 21. iV-(2-chloroethyl)-iV-nitrosoureido derivatives of cyclopentane- and cyclohexane-tetrols are mentioned in Chapter 18. Unsaturated glycosylated cyclitol derivatives are referred to in Chapter 12. 

The cyclopentane-based phosphate 79, designed as a mimic for myo-inositol 1,4,5-trisphosphate, has been synthesized by two different routes. The cyclitol ring was formed firstly by a Cp2Zr induced ring contraction of a hept-6-enose derivative, essentially as previously reported (Vol. 29, p. 238, ref. 94) secondly by a samarium diiodide promoted pinacol-like coupling of a 1,6-dialdehyde derived from methyl 2-0-benzyl-3,4-bis-(p-methoxybenzyl)-a-D-g/wco-hexodialdopyrano-side. ... 

Alditols, Cyclitols and Derivatives Thereof,- Meso-D- /ycero-L-a/tro-heptitol and its monohydratc and hcptaacetate, meso-D- /ycero-L-ido-heptitol and its heptaacetate, i,3,4,5-tetra-0-benzyl-p-D-fhictopyranosyl cyanide, 34 le cyclopropane fused carbocyclic nucleoside analogue 63, neplanocin intermediatB 64,the cyclopentane 65, l,3,S,7-tetraoxadecalins 66 and 67... 

Alditols, Cyclitols and Derivatives Thereof. - 2,5 3,4-Dianhydro-D-altritol, 2,5-aohydro-3,4-0-(l,2-ethanediyl)-D mannitol, pentaerythritol tetraacetate, ribitol tetraacetate, xylitol tetraacetate, D-arabinitol tetraacetate, D, L-arabinitol tetraacetate, 2,4 3,5-di-0-isopropylidene-D-mannitol, 2 hexa-O-acetyl-D-mannitol, allitol hexaacetate, D-mannitol hexaacetate, D, L-mannitol hexaacetate, D-iditol hexaacetate, D, L-iditol hexaacetate, D, L-glucitol hexaacetate, D, L-altritol hexaacetate, L-galacto-D-galacto-decitol (which is C2-symmetric), 5 6-0-benzyl-2,3-0-[(S)-caniphanylidene]-l,4,5-tris-0-pivaloyl-D-myo-inositol, 6D-3,6-di-0-benzyl-l-0-[(S)-camphanyl]-2-deoxy-2,2-difluoro-4,5-0-isopropylidene- y< -inositol, cyclopentane 28. ... 

Cyclopentane and Cyclobutane Derivatives.-The isolation of the unsaturated cyclitol 59 from Streptomyces citricolor has been described and proposed as a biosynthetic precursor of aristeromycin and neplanocin A. 

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