Pavan Kumar, K. V. P. ; Kumara Swamy, K. C. (2007) The first structural study on a cyclic tricoordinate phosphorochloridite and a pentacoordinate phosphorane based on 1,2,3,5-protected myo-inositol-a new conformation of 1,3,2-dioxaphosphorinane ring Carbohydrate Research, 342 (9). pp. 1182-1188. ISSN 0008-6215
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00086...
Related URL: http://dx.doi.org/10.1016/j.carres.2007.02.031
Abstract
Treatment of the phosphoramidite {myo-C6H6-2-[OC(O)Ph]-1,3,5-(O3CH)-4,6-(O2P-NH-i-Pr)} with o-chloranil affords the first example of inositol-based pentacoordinate phosphorane {myo-C6H6-2-[OC(O)Ph]-1,3,5-(O3CH)-4,6-(O2P-NH-i-Pr)(1,2-O2C6Cl4)} (9) (X-ray structure) with a trigonal bipyramidal geometry at phosphorus. The six-membered 1,3,2-dioxaphosphorinane ring with the inositol residue has an unusual boat conformation in 9 which is quite different from that found in unrestrained rings investigated before, but is similar to that of its PIII chloro precursor {myo-C6H6-2-[OC(O)Ph]-1,3,5-(O3CH)-4,6-(O2PCl)} (X-ray structure). Also, a convenient and chromatography-free procedure for the protected myo-inositol derivative {myo-C6H6-2-[OC(O)Ph]-1,3,5-(O3CH)-4,6-(OH)2} is reported.
Item Type: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
Keywords: | Myo-inositol; Conformation; Phosphoranes; Pentacoordinate; X-ray Structure |
ID Code: | 29655 |
Deposited On: | 23 Dec 2010 05:40 |
Last Modified: | 17 May 2016 12:28 |
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