The Selective Silylation of d‐Mannitol Assisted by Phenylboronic Acid and the Solid State and Solution Structures of the Intermediate 1,6‐bis(silyl) bis(phenylboronates)

References

• Ferrier , R. J. 1978 . Carbohydrate boronates . Adv. Carbohydr. Chem. Biochem. , 35 : 31 – 80 .
   Google Scholar
• Duggan , P. J. and Tyndall , E. M. 2002 . Boron acids as protective agents and catalysts in synthesis . J. Chem. Soc., Perkin Trans. 1 , : 1325 – 1339 .
   Google Scholar
• Bhaskar , V. , Duggan , P. J. , Humphrey , D. G. , Krippner , G. Y. , McCarl , V. and Offermann , D. A. 2001 . Phenylboronic acid as a labile protective agent: the selective derivatisation of 1,2,3‐triols . J. Chem. Soc., Perkin Trans. 1 , : 1098 – 1102 .
   Google Scholar
• Duggan , P. J. , Humphrey , D. G. , Price , D. and Tyndall , E. M. 2003 . 1,6‐Dibenzoyloxy‐2:4, 3:5‐O 2:O 4, O 3:O 5 bis(phenylboronoyloxy)‐d‐mannitol . Acta Crystallogr., E , 59 : o372 – o373 .
   Google Scholar
• Kocienski , P. J. 1994 . Protecting Groups Edited by: Enders , D. , Noyori , R. and Trost , B. M. 33 – 40 . Stuttgart : Thieme .
   Google Scholar
• Leigh , D. A. , Martin , R. P. , Smart , J. P. and Truscello , A. M. 1994 . Kinetically controlled regiospecific silylation of polyols via dibutylstannanediyl acetals . J. Chem. Soc., Chem. Commun. , : 1373 – 1374 .
   Google Scholar
• Downham , R. , Edwards , P. J. , Entwistle , D. A. , Hughes , A. B. , Kim , K. S. and Ley , S. V. 1995 . Dispiroketals in synthesis. Part 19. Dispiroketals as enantioselective and regioselective protective agents for symmetric cyclic and acyclic polyols . Tetrahedron: Asymmetry , 6 : 2403
   Google Scholar
• Iannazzo , D. , Piperno , A. , Pistara , V. , Rescifina , A. and Romeo , R. 2002 . Modified nucleosides. A general and diastereoselective approach to N,O‐psiconucleosides . Tetrahedron , 58 : 581
   Web of Science ®Google Scholar
• Gupta , B. A. , Kirfel , A. , Will , G. and Wulff , G. 1977 . The crystal structure of d‐mannitol tris(benzeneboronic) ester, C24H23B3O6 . Acta Crystallogr. , B33 : 637 – 641 .
   Google Scholar
• Salazar‐Pereda , V. , Martínez‐Martínez , L. , Flores‐Parra , A. , Rosales‐Hoz , M. D.J. , Ariza‐Castolo , A. and Contreras , R. 1994 . New phenylboronic esters derived from inositol . Heteroat. Chem. , 5 ( 2 ) : 139 – 143 .
   Google Scholar
• Ishi‐i , T. , Nakashima , K. , Shinkai , S. and Araki , K. 1998 . Structure determination of a 1:2 threitol‐boronic acid complex: comments on the structural controversy between 5,5‐ and 6,6‐membered rings . Tetrahedron , 54 : 8679 – 8686 .
   Google Scholar
• Gill , M. , Smrdel , A. F. , Strauch , R. J. and Begley , M. J. 1990 . Pigments of fungi. Part 12. Structure and absolute stereochemistry of antibiotic tetrahydroanthraquinones from the fungus dermocybe splendida horak. X‐ray structure determination of austrocortirubin phenylboronate and austrocortilutein acetonide . J. Chem. Soc., Perkin Trans. 1 , : 1583 – 1592 .
   Google Scholar
• Shimanouchi , H. , Saito , N. and Sasada , Y. 1969 . The crystal and molecular structure of N‐(p‐bromophenyl)‐α‐d‐ribopyranosylamine 2,4‐phenylboronate . Bull. Chem. Soc. Jpn. , 42 : 1239 – 1247 .
   Google Scholar
• Lide , D. R. and Frederikse , H. P.R. , eds. 1996 . CRC Handbook of Chemistry and Physics Vol. 77 , 1 – 9 . Boca Raton : CRC Press .
   Google Scholar
• Brauer , D. J. , Machnitzki , P. , Nickel , T. and Stelzer , O. 2000 . Water‐soluble phosphanes, 11. Syntheses and coordination chemistry of chiral phosphanyl glycerols and their derivatives‐X‐ray structure of (R)‐Ph2p‐Ch2‐C a H‐O‐B(Ph)‐O‐CbH2(C a –C b ) . Eur. J. Inorg. Chem. , : 65 – 73 .
   Google Scholar
• Sugihara , J. M. and Bowman , C. M. 1958 . Cyclic benzeneboronate esters . J. Am. Chem. Soc. , 80 : 2443 – 2446 .
   Google Scholar
• Kuivilla , H. G. , Keough , A. E. and Soboczenski , E. J. 1954 . Areneboronates from diols and polyols . J. Org. Chem. , 19 : 780 – 783 .
   Google Scholar
• Bellamy , L. J. , Gerrard , W. , Lappert , M. F. and Williams , R. L. 1958 . Infrared spectra of boron compounds . J. Chem. Soc. , : 2412 – 2415 .
   Google Scholar
• Farrugia , L. J. 1999 . Wingx‐Version 1.64.03b. An integrated system of windows programs for the solution, refinement and analysis of single crystal x‐ray diffraction data . J. Appl. Crystallogr. , 32 : 837 – 838 .
   Web of Science ®Google Scholar