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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 17
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Original Articles

Germanium (IV) chloride as catalyst for the protection of diols as cyclic orthoesters

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Pages 3179-3182 | Accepted 06 Feb 1998, Published online: 23 Aug 2006

References

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  • 1H-NMR (D2O, 300 MHz). α -methyl-galactopyranoside (diastereoisomeric mixture of protected substrate): δ: 1.42 and 1.58 (3H, s, CH3), 3.22 and 3.28 (3H, s, OCH3), 3.35 (3H, s, OCH3), 4.35 (2H, m, 2H-6), 4.80 (1H, m, H-4), 5.27 (1H, d, 6.5 Hz, H-1); 1H-NMR (CDCl3, 300 MHz). 1,2-hydroxy-2-phenyl-ethane (diastereoisomeric mixture of protected substrate): δ: 1.65 and 1.70 (3H, s, CH3), 3.35 and 3.40 (3H, s, OCH3), 3.75, 4.30 and 3.85, 4.45 (2H, ABX system), 5.10 and 5.25 (1H, ABX system, 7.40 (5H, Ph). Methyl quinate (diastereoisomeric mixture of protected substrate): δ: 1.59 and 1.60 (3H, s, CH3), 2.10, 2.35 and 2.05, 2.50 (2x2H, ABX system, 2H-2 and 2H-6), 3.26 and 3.41 (3H, s, OCH3), 3.55 (1H, m, H-5), 3.72 and 3.74 (3H, s, COOCH3–1), 4.60 (1H, m, H-3), 4.75 (1H, m, H-4), 5.25 (2H, bs, OH-1, OH-5).

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