Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 22
230
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Regioselective Acylation of Secondary Hydroxyl Groups by Means BOP‐Cl

, , , , &
Pages 4207-4217 | Received 19 Jan 2004, Published online: 10 Jan 2011

References

  • Hurford , J. R. 1980 . Developments in Food Carbohydrates Edited by: Lee , C. K. 327 – 334 . Barking, , UK : Applied Science Publishers .
  • Attwood , D. and Florence , A. T. 1983 . Surfactant Systems. Their Chemistry, Pharmacy and Biology London, , UK : Chapman and Hall .
  • Lichtenthaler , F. W. 1991 . Carbohydrates as Organic Raw Materials Edited by: Lichtenthaler , F. W. Weiheim, , Germany : VCH .
  • Ringsdorf , H. , Schlarb , B. and Venzmer , J. 1988 . Angew. Chem. Int. Ed. Engl. , 27 : 113
  • Lawrence , M. 1994 . J. Chem. Soc. Rev. , : 417 [CROSSREF]
  • Le Bec. , C. and Huynh‐Dinh , T. 1991 . Synthesis of lipophilic phosphate triester derivatives of 5‐fluorouridine and arabinocytidine as anticancer prodrugs . Tetrahedron Lett. , 32 : 6553 [CROSSREF]
  • Dasgupta , F. , Hay , G. W. , Szareck , W. A. and Shilling , W. L. 1983 . Acetylation of carbohydrates by transesterification using ethyl acetate and sodium hydride . Carbohydr. Res. , 114 : 153 [CROSSREF]
  • Plusquellec , D. and Baczko , K. 1987 . Sugar chemistry without protecting groups: a novel regioselective synthesis of 6‐O‐acyl‐D‐glucopyranoses and methyl‐6‐O‐acyl‐α‐D‐glucopyranosides . Tetrahedron Lett. , 28 : 3809 [CROSSREF]
  • Baczko , K. and Plusquellec , D. 1991 . Sugar chemistry without protecting groups‐III. A facile chemical synthesis of 6‐O‐acyl‐D‐glycopyranoses and methyl‐6‐O‐acyl‐d‐glycopyranosides . Tetrahedron , 47 : 3817 [CROSSREF]
  • De Luca , D. , De Nino , A. , Liguori , A. , Procopio , A. and Sindona , G. 1997 . Nonionic surfactants regioselective synthesis of fatty acid esters of α‐ and β‐glucopyranose . Lipids , 32 ( 5 ) : 559 [PUBMED] [INFOTRIEVE] [CSA]
  • De Nino , A. , Liguori , A. , Procopio , A. , Roberti , E. and Sindona , G. 1996 . A novel approach to the synthesis of lipophilic thymidinemonophosphoglucopyranosides as drug delivery systems . Carbohydr. Res. , 286 : 77 [CROSSREF]
  • Brown , J. M. , Christodolou , C. , Reese , C. B. and Sindona , G. 1984 . Two new protected acyl protecting groups for alcoholic hydroxy functions . J. Chem. Soc., Perkin Trans. 1. , : 1785 [CROSSREF]
  • Liguori , A. , Perri , E. , Sindona , G. and Uccella , N. 1988 . Chemo and regioselective acylation of deoxyribonucleosides by means of N,N‐bis‐(2‐oxo‐oxazolidin‐3‐yl) phosphorodiammidic chloride (BOPDC) . Tetrahedron , 44 : 229 – 234 . [CROSSREF]
  • Liguori , A. , Procopio , A. , Romeo , G. , Sindona , G. and Uccella , N. 1993 . Regioselective acylation of methyl α‐D‐glucopyranoside and methyl α‐D‐mannopyranoside by means of bis(2‐oxooxazolidin‐3‐yl)phosphinic chloride (BOP‐Cl) . J. Chem. Soc. Perkin Trans. 1. , : 1783 [CROSSREF]
  • De Nino , A. , Leggio , A. , Liguori , A. , Maiuolo , L. , Napoli , A. , Procopio , A. , Roberti , E. , Siciliano , C. and Sindona , G. 1996 . Regioselective synthesis of aminoacylthymidines by direct esterification with bis (2‐oxooxazolidin‐3‐yl) phosphinic chloride (BOP‐Cl) . Gazz. Chim. Ital. , 126 : 605
  • Cabrè , J. and Palomo , A. L. 1984 . New experimental strategies in amide synthesis using N,N‐Bis[2‐oxo‐3‐oxazolidinyl]phosphorodiamidic chloride . Synthesis , : 413
  • Ohle , H. and Tessmar , K. 1938 . Syntheses with 5,6‐anhydroacetoneglucose. (VI). 6‐alkyl ethers of glucose . Ber. , 71B : 1843 (Chem. Abst. 32: 9043)
  • Chaudhary , S. K. and Hernandez , O. 1979 . A simplified procedure for the preparation of triphenylmethylethers . Tetrahedron Lett. , 20 : 95 [CROSSREF]
  • Weinmann , G. and Khorana , H. G. 1962 . Studies on polynucleotides. XIII.1 Stepwise synthesis of deoxyribo‐oligonucleotides. An alternative general approach and the synthesis of thymidine di‐, tri‐ and tetranucleotides bearing 3″‐posphomonoester end groups2 . J. Am. Chem. Soc. , 84 : 419
  • Williams , J. M. and Richardson , A. C. 1967 . Selective acylation of pyranoside—I. Benzoylation of methyl α‐D‐glycopyranosides of mannose, glucose and galactose . Tetrahedron , 23 : 1369 [CROSSREF]
  • Peri , F. , Cipolla , L. and Nicotra , F. 2000 . Tin‐mediated regioselective acylation of unprotected sugars on solid phase . Tetrahedron Lett. , 41 : 8587 [CROSSREF]
  • Therisold , M. and Klibanov , A. M. 1986 . Facile enzymatic preparation of monoacylated sugars in pyridine . J. Am. Chem. Soc. , 108 : 5638
  • Therisold , M. and Klibanov , A. M. 1987 . Regioselective acylation of secondary hydroxyl groups in sugars catalyzed by lipases in organic solvents . J. Am. Chem. Soc. , 109 : 3977
  • MacManus , D. A. and Vulfson , E. N. 1995 . Substituent effects on the regioselectivity of enzymatic acylation of 6‐O‐alkylglycopyranosides using Pseudomonas cepacia lipase . Carbohydr. Res. , 279 : 281 [CROSSREF]
  • Bessodes , N. , Komiotis , D. and Antonakis , K. 1986 . Rapid and selective detritylation of primary alcohols using formic acid . Tetrahedron Lett. , : 579 [CROSSREF]
  • Köster , H. and Sinha , N. D. 1982 . Dialkyl aluminium chloride: a reagent for removal of trityl group from trityl ethers of deoxynucleosides, deoxynucleotides, and oligodeoxynucleotides . Tetrahedron Lett. , 23 : 2641 [CROSSREF]
  • Jackson , A. E. and Johnstone , R. A.W. 1976 . Rapid, selective removal of benzyloxycarbonyl groups from peptides by catalytic transfer hydrogenation . Synthesis , : 685 [CROSSREF]
  • Brieger , G. and Nestrick , T. 1974 . J. Catalytic transfer hydrogenation. Chem. Rev. , 74 : 567

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.