A Facile, One‐Step Conversion of 6‐O‐Trityl and 6‐O‐TBDMS Monosaccharides into the Corresponding Formate Esters

References

• Jarosz , S. and Mach , M. 2002 . Regio‐ and stereoselective transformations of sucrose at the terminal positions . Eur. J. Org. Chem. , : 769 – 780 .
   Google Scholar
• Franke , F. and Guthrie , R. D. 1977 . Tert‐butyldimethylsilyl ethers of sucrose . Aust. J. Chem. , 30 : 639 – 647 .
   Web of Science ®Google Scholar
• Prakash , C. , Saleh , S. and Blair , I. A. 1994 . Selective removal of phenolic and alcoholic silyl ethers . Tetrahedron Lett. , 35 : 7565 – 7568 .
   Web of Science ®Google Scholar
• Maiti , G. and Roy , S. C. 1997 . A mild and efficient method for the selective cleavage of tert‐butyldimethylsilyl ethers to alcohols . Tetrahedron Lett. , 38 : 495 – 498 .
   Web of Science ®Google Scholar
• DeLuca , L. , Giacomelli , G. and Porcheddu , A. 2002 . Mild and highly selective formyl protection of primary hydroxyl groups . J. Org. Chem. , 67 : 5152 – 5155 .
   Google Scholar
• Zemlicka , J. , Beranek , J. and Smrt , J. 1962 . Preparation and methanolysis of uridine, 6‐azauridine and 6‐azacytidine O‐formyl derivatives . Collect. Czech. Chem. Commun. , 27 : 2784
   Google Scholar
• Reese , C. B. and Stewart , J. C.M. 1968 . Methoxyacetyl as a protecting group in ribonucleoside chemistry . Tetrahedron Lett. , : 4273 – 4276 .
   Google Scholar
• Ringold , H. J. , Loken , B. , Rosenkranz , G. and Sondheimer , F. 1956 . The direct oppenauer oxidation of steroidal formate esters . J. Am. Chem. Soc. , 78 : 816 – 819 .
   Web of Science ®Google Scholar
• Ringold , H. J. , Rosenkranz , G. and Sondheimer , F. 1956 . Synthesis Δ4‐pregnene‐17α,21‐diol‐3,20dione (Reichstein's Substance S) and Δ1,4‐pregnadiene‐17α,21‐diol‐3,20‐dione . J. Am. Chem. Soc. , 78 : 820 – 825 .
   Google Scholar
• Suda , M. 1982 . Short‐step syntheses of (±)bazzanene and (±)trichodiene . Tetrahedron Lett. , : 427 – 428 .
   Google Scholar
• Mandai , T. , Osaka , K. , Kawagishi , M. , Kawada , M. and Otera , J. 1984 . Synthesis and highly regioselective diels‐alder reaction of functionalized isoprenes involving a terminal alkoxy group and chemical modification of the resulting adducts . J. Org. Chem. , 49 : 3595 – 3600 .
   Google Scholar
• Mandai , T. , Matsumoto , T. , Kawada , M. and Tsuji , J. 1992 . Stereocontolled formation of cis and trans ring junctions in hydrindane and decalin systems by palladium‐catalyzed regioselective hydrogenolysis of allylic formates . J. Org. Chem. , 57 : 1326 – 1327 .
   Google Scholar
• Ali , B. E. and Alper , H. 1995 . Regioselective palladium(II) catalysed hydroesterification of alkynes and alkynols using formate esters . J. Mol. Catal. A , 96 : 197 – 201 .
   Web of Science ®Google Scholar
• Subramanyam , V. and Silver , E. H. 1976 . Reaction of phosphoranes with formate esters. A new method for the synthesis of vinyl ethers . J. Org. Chem. , 41 : 1272 – 1273 .
   Google Scholar
• Strazzolini , P. , Giumanini , A. G. and Cauci , S. 1990 . Acetic formic anhydride a review . Tetrahedron , 46 : 1081 – 1118 .
   Web of Science ®Google Scholar
• Katritzky , A. R. , Chang , H. X. and Yang , B. 1995 . N‐Formylbenzotriazole – a stable and convenient N‐formylating and O‐formylating agent . Synthesis , : 503 – 505 .
   Google Scholar
• Barluenga , J. , Campos , P. J. , Gonzales‐Nunez , E. and Asensio , G. 1985 . General‐method for the formylation of alcohols with dimethylformamide – an extension of the Vilsmeier‐Haack reaction . Synthesis , : 426 – 428 .
   Google Scholar
• Olah , G. A. , Ohannesian , L. and Arvanaghi , M. 1987 . Synthetic methods and reactions. 130 . Formylating agents. Chem. Rev. , 87 : 671 – 686 .
   Web of Science ®Google Scholar
• Hagiwara , H. , Morohashi , K. , Sakai , H. , Suzuki , T. and Ando , M. 1998 . Acetylation and formylation of alcohols with triphenylphosphine and carbon tetrabromide in ethyl acetate or ethyl acetate or ethyl formate . Tetrahedron , 54 : 5845 – 5852 .
   Web of Science ®Google Scholar
• Koeller , S. and Lellouche , J. P. 1999 . Preparation of formate esters from O‐TBDMS/O‐TES protected alcohols. A one‐step conversion using the Vilsmeier‐Haack complex POCl3/DMF . Tetrahedron Lett. , 40 : 7043 – 7046 .
   Web of Science ®Google Scholar
• Lellouche , J. P. and Koeller , S. 2001 . The particular sensitivity of silyl ethers of D‐glucal toward two Vilsmeier‐Haack reagents POCl3/DMF and (CF3SO2)2O/DMF. Their unique and selective conversion to the corresponding C(6)‐O‐formates . J. Org. Chem. , 66 : 693 – 696 .
   PubMed Web of Science ®Google Scholar
• Lellouche , J. P. and Kotlyar , V. 2004 . Vilsmeier‐Haack reagents. Novel electrophiles for the one‐step formylation of O‐silylated ethers to O‐formates . Synlett. , 3 : 564 – 571 .
   Google Scholar
• Andrade , M. M. and Barros , M. T. 2004 . Facile conversion of O‐silyl protected sugars into their corresponding formates using POCl3/DMF complex . Tetrahedron , 60 : 9235 – 9243 .
   Web of Science ®Google Scholar
• Kovac , P. , Sokoloski , E. A. and Glaudemans , C. P.J. 1984 . Synthesis and characterization of methyl 6‐O‐α‐ and ‐β‐D‐galactopyranosyl‐β‐D‐galactopyranoside . Carbohydr. Res. , 128 : 101 – 110 .
   PubMed Web of Science ®Google Scholar
• Gros , E. G. and Gruneiro , E. M. 1970 . Methylation of carbohydrates bearing base‐labile substituents, with diazomethane‐boron trifluoride etherate . Carbohydr. Res. , 14 : 409 – 411 .
   Web of Science ®Google Scholar
• Horton , D. and Lauterback , J. H. 1969 . Pelative reactivities of hydroxyl groups in carbohydrate derivatives. Specific nuclear magnetic resonance spectral assignments of acetyl groups in methyl α‐D‐glucopyranoside tetraacetate and related derivatives . J. Org. Chem. , 34 : 86 – 92 .
   Web of Science ®Google Scholar
• Bessodes , M. , Komiotis , D. and Antonakis , K. 1986 . Rapid and selective detritylation of primary alcohols using formic acid . Tetrahedron Lett. , 27 : 579 – 580 .
   Web of Science ®Google Scholar
• Trippet , S. and Walker , D. M. 1961 . The phosphobetaines: preparation and properties . J. Chem. Soc. , : 1266 – 1272 .
   Google Scholar
• Dondoni , A. 2000 . Formylation of carbohydrates and the evolution of synthetic routes to artificial oligosacharides and glycoconjugates . Pure Appl. Chem. , 72 : 1577 – 1588 .
   Google Scholar
• Aburto , J. , Alric , I. and Borredon , I. 1999 . Preparation of long‐chain esters of starch using fatty acid chlorides in the absence of an organic solvent . Starch/Starke , 51 : 132 – 135 .
   Google Scholar
• Kieburg , C. , Sadalapure , K. and Lindhorst , T. K. 2000 . Glucose‐based AB2‐building blocks for the construction of branched glycopeptidomimetics . Eur. J. Org. Chem. , : 2035 – 2040 .
   Google Scholar
• Wong , C. H. , Moris‐Varas , F. , Hung , S. C. , Marron , T. G. , Lin , C. C. , Gong , K. W. and Weitz‐Schmidt , G. 1997 . Small molecules as structural and functional mimics of sialyl Lewis X tetrasaccharide in slectin inhibition: a remarkable enhancement of inhibition by additional negative charge and/or hydrophobic group . J. Am. Chem. Soc. , 119 : 8152 – 8158 .
   Google Scholar
• Arsequell , G. and Valencia , G. 1997 . O‐glycosyl α‐amino acids as building blocks for glycopeptide synthesis . Tetrahedron: Assymm. , 8 : 2839 – 2876 .
   Google Scholar
• Taylor , C. M. 1998 . Glycopeptides and glycoproteins: focus on the glycosidic linkage . Tetrahedron , 54 : 11317 – 11362 .
   Web of Science ®Google Scholar
• Pellissier , H. 2005 . Use of O‐glycosylation in total synthesis . Tetrahedron , 61 : 2947 – 2993 .
   Google Scholar
• Xing , G. W. , Wu , D. , Poles , M. A. , Horowitz , A. , Tsuji , M. , Ho , D. D. and Wong , C. H. 2005 . Synthesis and human NKT cell stimulating properties of 3‐O‐sulfo‐α/β‐galactosylceramides . Bioorg. Med. Chem. , 13 : 2907 – 2916 .
   Google Scholar