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9
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0028330925
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For previous asymmetric syntheses of conduritol E: (a) Takano, S.; Yoshimitsu, T.; Ogasawara, K. J. Org. Chem. 1994, 59, 54. (b) Hudlicky, T.; Luna, H.; Olivo, H. F.; Andersen, C.; Nugent, T.; Price, J. D. J. Chem. Soc., Perkin Trans. 1 1991, 2907. For a previous asymmetric synthesis of 2-deoxy-allo-inositol: (c) McCasland, G. E.; Furuta, S.; Johnson, L. F.; Shoolery, J. N. J. Am. Chem. Soc. 1961, 83, 2335. (d) Angyal, S. J.; Odier, L. Carbohydr. Res. 1982, 101, 209. (e) Angyal, S. J.; Odier, L. Ibid. 1982, 100, 43.
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Takano, S.1
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10
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37049088912
-
-
For previous asymmetric syntheses of conduritol E: (a) Takano, S.; Yoshimitsu, T.; Ogasawara, K. J. Org. Chem. 1994, 59, 54. (b) Hudlicky, T.; Luna, H.; Olivo, H. F.; Andersen, C.; Nugent, T.; Price, J. D. J. Chem. Soc., Perkin Trans. 1 1991, 2907. For a previous asymmetric synthesis of 2-deoxy-allo-inositol: (c) McCasland, G. E.; Furuta, S.; Johnson, L. F.; Shoolery, J. N. J. Am. Chem. Soc. 1961, 83, 2335. (d) Angyal, S. J.; Odier, L. Carbohydr. Res. 1982, 101, 209. (e) Angyal, S. J.; Odier, L. Ibid. 1982, 100, 43.
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Olivo, H.F.3
Andersen, C.4
Nugent, T.5
Price, J.D.6
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11
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0001517733
-
-
For previous asymmetric syntheses of conduritol E: (a) Takano, S.; Yoshimitsu, T.; Ogasawara, K. J. Org. Chem. 1994, 59, 54. (b) Hudlicky, T.; Luna, H.; Olivo, H. F.; Andersen, C.; Nugent, T.; Price, J. D. J. Chem. Soc., Perkin Trans. 1 1991, 2907. For a previous asymmetric synthesis of 2-deoxy-allo-inositol: (c) McCasland, G. E.; Furuta, S.; Johnson, L. F.; Shoolery, J. N. J. Am. Chem. Soc. 1961, 83, 2335. (d) Angyal, S. J.; Odier, L. Carbohydr. Res. 1982, 101, 209. (e) Angyal, S. J.; Odier, L. Ibid. 1982, 100, 43.
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McCasland, G.E.1
Furuta, S.2
Johnson, L.F.3
Shoolery, J.N.4
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12
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0013555886
-
-
For previous asymmetric syntheses of conduritol E: (a) Takano, S.; Yoshimitsu, T.; Ogasawara, K. J. Org. Chem. 1994, 59, 54. (b) Hudlicky, T.; Luna, H.; Olivo, H. F.; Andersen, C.; Nugent, T.; Price, J. D. J. Chem. Soc., Perkin Trans. 1 1991, 2907. For a previous asymmetric synthesis of 2-deoxy-allo-inositol: (c) McCasland, G. E.; Furuta, S.; Johnson, L. F.; Shoolery, J. N. J. Am. Chem. Soc. 1961, 83, 2335. (d) Angyal, S. J.; Odier, L. Carbohydr. Res. 1982, 101, 209. (e) Angyal, S. J.; Odier, L. Ibid. 1982, 100, 43.
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Angyal, S.J.1
Odier, L.2
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13
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0002780895
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For previous asymmetric syntheses of conduritol E: (a) Takano, S.; Yoshimitsu, T.; Ogasawara, K. J. Org. Chem. 1994, 59, 54. (b) Hudlicky, T.; Luna, H.; Olivo, H. F.; Andersen, C.; Nugent, T.; Price, J. D. J. Chem. Soc., Perkin Trans. 1 1991, 2907. For a previous asymmetric synthesis of 2-deoxy-allo-inositol: (c) McCasland, G. E.; Furuta, S.; Johnson, L. F.; Shoolery, J. N. J. Am. Chem. Soc. 1961, 83, 2335. (d) Angyal, S. J.; Odier, L. Carbohydr. Res. 1982, 101, 209. (e) Angyal, S. J.; Odier, L. Ibid. 1982, 100, 43.
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Angyal, S.J.1
Odier, L.2
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35
-
-
3643099302
-
-
note
-
Ten to 20% of the corresponding siloxane is sometimes produced during the workup but is easily removed by distillation. The amount of siloxane can be reduced by diluting the reaction mixture prior to aqueous workup.
-
-
-
-
36
-
-
0042398536
-
-
2: Andrianov, K. A.; Delazari, N. V. Dok. Akad. Nauk. SSSR 1958, 122, 393; Chem. Abst. 1959, 53, 2133.
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Andrianov, K.A.1
Delazari, N.V.2
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37
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84943847437
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-
2: Andrianov, K. A.; Delazari, N. V. Dok. Akad. Nauk. SSSR 1958, 122, 393; Chem. Abst. 1959, 53, 2133.
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-
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38
-
-
85088232376
-
-
note
-
4Cl.
-
-
-
-
39
-
-
3643104570
-
-
note
-
The reaction between 3a and AD-mix was complete after 12 h at 0°C and led after careful extraction to the desired 1,2-diol in 65-75% crude yield. The presence of more polar, intractable tetrols in the aqueous phase cannot, however, be excluded.
-
-
-
-
40
-
-
3643074390
-
-
note
-
DMF was used instead of the standard THF-MeOH mixture, which led to incomplete oxidation.
-
-
-
-
41
-
-
85088228769
-
-
note
-
1H NMR of Mosher's esters.
-
-
-
-
44
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-
33845557645
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-
(b) Morgans, D. J., Jr.; Sharpless, K. B.; Traynor, S. G. J. Am. Chem. Soc. 1981, 103, 462.
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Morgans Jr., D.J.1
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Traynor, S.G.3
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46
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0001700599
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Lohray, B. B.; Gao, Y.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 2623.
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Lohray, B.B.1
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Sharpless, K.B.3
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47
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0030058156
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