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This compound was first synthesized by Ogawa's group: Sato, S.; Nunomura, S.; Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 4097. The low overall yield and length (14 steps) of the synthesis, however, prompted us to develop a shorter, more efficient synthesis of this compound: Lassaletta, J. M.; Schmidt, R. R. Synlett 1995, 925.
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This compound was first synthesized by Ogawa's group: Sato, S.; Nunomura, S.; Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 4097. The low overall yield and length (14 steps) of the synthesis, however, prompted us to develop a shorter, more efficient synthesis of this compound: Lassaletta, J. M.; Schmidt, R. R. Synlett 1995, 925.
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16044373072
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note
-
This compound was obtained in good yield by direct anomeric O-alkylation of 4,6-O-benzylidenegalactopyranose (see Experimental Section).
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41
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16044370511
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note
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Though the phosphite methodology (see ref 19) usually yields virtually complete α-selectivities, other rather unpredictable results have been observed for related systems. This result, however, can be considered as acceptable due to the high yield obtained.
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42
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0001485197
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a) δ 3-Heq(α) > δ 3-Heq(β): Dabrowski, U.; Friebolin, H.; Brossmer, R.; Supp, M. Tetrahedron Lett. 1979, 4637.
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46
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16044366293
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note
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1H NMR data reported for SGG in ref 18 are erroneous.
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