153607-80-8

Usage

Uses

Used in Organic Synthesis:
(1S,5R)-3-(3α-hydroxy-6,8-dioxabicyclo[3.2.1]octan-3-yl)benzyl alcohol is used as a building block for the synthesis of other chemical compounds due to its unique structure and stereochemistry.
Used in Pharmaceutical Research:
(1S,5R)-3-(3α-hydroxy-6,8-dioxabicyclo[3.2.1]octan-3-yl)benzyl alcohol is used as a target for further study and potential applications in various fields of chemistry and biology, including pharmaceutical research.
Used in Chemical Research:
(1S,5R)-3-(3α-hydroxy-6,8-dioxabicyclo[3.2.1]octan-3-yl)benzyl alcohol is used as an interesting target for further study in the field of chemistry, given its complex bicyclic structure and stereochemistry.

Upstream product

• 167841-03-4 (1S,3S,5R)-3-[3-(tert-Butyl-diphenyl-silanyloxymethyl)-phenyl]-6,8-dioxa-bicyclo[3.2.1]octan-3-ol 
• 2280-44-6 D-Glucose 
• 14241-58-8 (1R,3S,5S)-6,8-dioxabicyclo[3.2.1]octan-3-ol 
• 20204-80-2 [(1R,2S,3S,4R,5R)-3-hydroxy-4-(p-tolylsulfonyl)-6,8-dioxabicyclo[3.2.1]oct-2-yl]-4-methylbenzenesulfonic acid 
• 30923-34-3 1,6-anhydro-2,4-dideoxy-β-D-glycero-hexopyranos-3-ulose 

Relevant academic research and scientific papers

Dioxabicyclooctanyl naphthalenenitriles as nonredox 5-lipoxygenase inhibitors: Structure-activity relationship study directed toward the improvement of metabolic stability

Naphthalenic lignan lactone 3a (L-702,539), a potent and selective 5- 1ipoxygenase (5-LO) inhibitor, is extensively metabolized at two different sites: the tetrahydropyran and the lactone rings. Early knowledge of the metabolic pathways triggered and directed a structure-activity relationship study aimed toward the improvement of metabolic stability in this series. The best modifications discovered, i.e., replacement of the lactone ring by a nitrile group, replacement of the tetrahydropyran ring by a 6,8- dioxabicyclo[3.2.1]octanyl moiety, and replacement of the pendant phenyl ring by a 3-furyl ring, were incorporated in a single molecule to produce inhibitor 9ac (L-708,780). Compound 9ac inhibits the oxidation of arachidonic acid to 5-hydroperoxyeicosatetraenoic acid by 5-LO (IC50 = 190 nM) and the formation of leukotriene B4 in human polymorphonuclear leukocytes (IC50 = 3 nM) as well as in human whole blood (IC50 = 150 nM). The good inhibitory profile shown by naphthalenenitrile 9ac is accompanied by an improved resistance to oxidative metabolism. In addition, 9ac is orally active in the functional model of antigen-induced bronchoconstriction in allergic squirrel monkeys (95% inhibition at 0.1 mg/kg).