Transformation of quercitols into 4-methylenecyclohex-5-ene-1,2,3-triol derivatives, precursors for the chemical chaperones N-octyl-4-epi-β-valienamine (NOEV) and N-octyl-β-valienamine (NOV).

Abstract:

:(+)-proto-Quercitol (1) and (-)-vibo-quercitol (2), both of which could be readily prepared by the bioconversion of myo-inositol, were successfully converted into the corresponding 4-methylenecyclohex-5-ene-1,2,3-triol derivatives. These compounds were demonstrated to be suitable precursors, preserving their configurations, for bioactive carba-aminosugars such as the potent chemical chaperone drug candidates, N-octyl-4-epi-β-valienamine (NOEV, 3) and N-octyl-β-valienamine (NOV, 4).

journal_name

Bioorg Med Chem Lett

authors

Kuno S,Takahashi A,Ogawa S

doi

10.1016/j.bmcl.2011.09.067

subject

Has Abstract

pub_date

2011-12-01 00:00:00

pages

7189-92

issue

23

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(11)01311-4

journal_volume

21

pub_type

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