Regioselective synthesis of C-nucleosides by 1, 3-dipolar cycloaddition of arylnitrile oxides to 5, 6-dideoxy-1, 2-O-iso-propylidene-α-d-xylo-hex-5-enofuranose
UAR Al-Timari, Ľ Fišera
Index: Al-Timari, Usama A. R.; Fisera, Lubor Carbohydrate Research, 1991 , vol. 218, # 1 p. 121 - 127
Full Text: HTML
Citation Number: 16
Abstract
Abstract 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 (⩾ 95% π-facial stereoselectivity).
Related Articles:
Copper (II)-mediated oxidation of 1, 2-dioxime to furoxan
[Das, Oindrila; Paria, Sayantan; Paine, Tapan Kanti Tetrahedron Letters, 2008 , vol. 49, # 41 p. 5924 - 5927]
The conversion of α-keto acids and of α-keto acid oximes to nitriles in aqueous solution
[Arai, Noriyoshi; Iwakoshi, Mitsuhiko; Tanabe, Katsuhiko; Narasaka, Koichi Bulletin of the Chemical Society of Japan, 1999 , vol. 72, # 10 p. 2277 - 2285]
[Kelly, David R.; Baker, Simon C.; King, David S.; Silva, Deepa S. de; Lord, Gwyn; Taylor, Jason P. Organic and Biomolecular Chemistry, 2008 , vol. 6, # 6 p. 787 - 796]
Mechanistic impact of oxime formation accompanying 1, 3-dipolar cycloadditions of nitrile oxides
[Baran, Janusz; Mayr, Herbert Journal of Organic Chemistry, 1989 , vol. 54, # 21 p. 5012 - 5016]
The Reaction of Sodium Nitrite with Ethyl Bromoacetate and with Benzyl Bromide1, 2
[Kornblum; Weaver Journal of the American Chemical Society, 1958 , vol. 80, p. 4333,4337]