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66149185340
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The stereochemistry of 5a was established by the advanced Mosher method, see Supporting Information.
-
The stereochemistry of 5a was established by the advanced Mosher method, see Supporting Information.
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35
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9244244705
-
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Ti(OiPr)4 is known to form Ti-oxo species such as [Ti7O4](OR)20, [Ti8O6](OR)20, and [Ti12O16](OR)16 with trace amount of water through Ti(OiPr)3(OH), see: Hubert-Pfalzgraf, L. G. J. Mater. Chem. 2004, 14, 3113.
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Ti(OiPr)4 is known to form Ti-oxo species such as [Ti7O4](OR)20, [Ti8O6](OR)20, and [Ti12O16](OR)16 with trace amount of water through Ti(OiPr)3(OH), see: Hubert-Pfalzgraf, L. G. J. Mater. Chem. 2004, 14, 3113.
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66149190594
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We are currently investigating a chiral reagent which promotes the reaction of 4 to 5a with high yield and high selectivity
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We are currently investigating a chiral reagent which promotes the reaction of 4 to 5a with high yield and high selectivity.
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39
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66149164358
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Addition of pyridine was indispensable for successful inversion of the C5′-stereocenter of 5b with ClCH2CO2H.
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Addition of pyridine was indispensable for successful inversion of the C5′-stereocenter of 5b with ClCH2CO2H.
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40
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66149176838
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The orthoester 7 shows a characteristic chemical shift of 1.78 ppm (CH3) in the 1H NMR spectrum.
-
The orthoester 7 shows a characteristic chemical shift of 1.78 ppm (CH3) in the 1H NMR spectrum.
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43
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66149160284
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Due to the fact that all triflate ion associated glycosylations with 6(entries 1-3) yielded a mixture of R-and-mannosides, the mannosyl carbenium ion generated directly from 6 or through the orthoester 7 would be transformed to the R-glycosyl triflate which furnishes the undesired-mannoside 8b.
-
Due to the fact that all triflate ion associated glycosylations with 6(entries 1-3) yielded a mixture of R-and-mannosides, the mannosyl carbenium ion generated directly from 6 or through the orthoester 7 would be transformed to the R-glycosyl triflate which furnishes the undesired-mannoside 8b.
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44
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0022626632
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The formation of orthoesters had previously been reported with a number of different glycosyl donors which react through an oxonium ion intermediate and contain a C2-acetyl group, see: Harreus, A. H, Kunz, H. Liebigs Ann. Chem 1986, 717
-
The formation of orthoesters had previously been reported with a number of different glycosyl donors which react through an oxonium ion intermediate and contain a C2-acetyl group, see: Harreus, A. H.; Kunz, H. Liebigs Ann. Chem 1986, 717.
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48
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84868945306
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The isolated orthoester 7 could be rearranged to 8a by the treatment with HBF4·OEt2 compex in CH2Cl2.
-
The isolated orthoester 7 could be rearranged to 8a by the treatment with HBF4·OEt2 compex in CH2Cl2.
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-
50
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84868936849
-
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Deprotection of the BOM-protected 13 under these conditions was ∼40% yield.
-
Deprotection of the BOM-protected 13 under these conditions was ∼40% yield.
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0035800459
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53
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66149162992
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See Supporting Informataion
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See Supporting Informataion.
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