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3 derivatives with almost complete retention of configuration as well as high chemoselectivity. See, the references 10 and 11.
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note
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Calculations were performed by MOPAC v 6.10 (AM1) implemented in CAChe Worksystem (SONY/Tektronix Corporation) for the conformers obtained from the rigid search method followed by the optimization by the eigenvector following minimization (EF) method with the extra keyword "PRECISE", final gradient norm being less than 0.01 kcal/Å.
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41
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1842436048
-
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note
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- (MNDO: 1.735 Å, AM1: 1.654 Å, PM3: 1.918 Å), to the one obtained by ab initio calculations (HF/3-21G: 1.523 Å, HF/6-31G*: 1.529 Å, MP2/6-31G*: 1.529 Å). MOPAC, in the calculation of this alkoxide, tends to give longer and shorter bond lengths for C-C and C-O with the difference of 0.13∼0.39 Å and 0.04∼0.06 Å, respectively.
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1842488366
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note
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Reaction temperature would also be the important factor because, as shown in the text, LAH reduction was conducted at 0°C, while the mixture was cooled to -78°C for DIBALH reduction.
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49
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0000969892
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Previously, the similar type of compounds were synthesized in a isolated yield range of 70 to 80%. See, Hanzawa, Y.; Kawagoe, K.; Tanahashi, N.; Kobayashi, Y. Tetrahedron Lett. 1984, 25, 4749.
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1842488365
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Sugar numbering system was used
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Sugar numbering system was used.
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1842540386
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