Regioselective synthesis of C-nucleosides by 1,3-dipolar cycloaddition of arylnitrile oxides to 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

DOI: 10.1016/0008-6215(91)84091-R

Source and publish data:

Carbohydrate Research p. 121 - 127 (1991)

Update date:2022-08-05

Topics:

Authors:

Al-Timari, Usama A. R.

Fisera, Lubor

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Article abstract of DOI:10.1016/0008-6215(91)84091-R

The synthesis of 3-aryl-5-(1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-2-isoxazoline (3) from arylnitrile oxides and 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (1) is described.The 1,3-dipolar cycloaddition reactions give mainly anti-adducts (>=95percent ?-facial stereoselectivity).

Full text of DOI:10.1016/0008-6215(91)84091-R

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Product name:(3aR,5S,6S,6aR)-5-((S)-3-Benzo[1,3]dioxol-5-yl-4,5-dihydro-isoxazol-5-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

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