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Efficient syntheses of (−)-shikimate and (−)-quinate 3-phosphate via trans vicinal diol protection with 2,2,3,3-tetramethoxybutane (TMB) of shikimic and quinic acids

✍ Scribed by Tzenge-Lien Shih; Shih-Hsiung Wu *

Book ID: 104210133
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 97 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00280-x

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✦ Synopsis

Shikimate 3-phosphate and (-)-quinate 3-phosphate can be synthesized by selective protection of their trans diol functionality using 2,2,3,3-tetramethoxybutane (TMB) using D-(-)-shikimic acid and D-(-)-quinic acid as starting materials. This versatile reagent facilitates the synthesis of these important biological targets in fewer steps than previously reported. By the proper choice of protecting group for C-3 hydroxyl in D-(-)-quinic acid, it can be converted to a key intermediate in the synthesis of (-)-shikimate 3-phosphate.

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