Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/76473
Title: Mercuricyclisation of D-erythro-hept-1,3-dienitol: Reductive demercuriation in the presence and absence of oxygen
Authors: Lee, C.K. 
Jiang, H. 
Keywords: (1,3,5-tri-O-benzyl-β-D-arabino- and ribo- furanosyl)ethene
3,7-dibenzyloxy-hept-1,3,5-triene-6- ol
Borohydride-induced oxidation
D-erythro-hept-1,3-dienitol
Mercuri- cyclisation
Oxymercuriation-demercuriation
Issue Date: 1999
Source: Lee, C.K.,Jiang, H. (1999). Mercuricyclisation of D-erythro-hept-1,3-dienitol: Reductive demercuriation in the presence and absence of oxygen. Carbohydrate Letters 3 (5) : 309-315. ScholarBank@NUS Repository.
Abstract: Treatment of 3,5,7-tri-O-benzyl-D-erythro-hept-1,3-dienitol with mercuric acetate or trifluoromethanesulfonate followed by aqueous potassium chloride, produced (1,3,5-tri-O-benzyl-2-deoxy-2-chloromercurio-β-D- arabinofuranosyl)ethene (2) as the only isolated product. Reductive demercuriation of the chloromercurio-ether 2 in the presence of molecular oxygen gave a mixture of 3,7-dibenzyloxy-hept-1,3,5-triene-6-ol (3), (1,3,5- tri-O-benzyl-β-D-arabinofuranosyl)ethene (4) and D-ribofuranosyl)ethene (5). Compound 3 was obtained as the major product when the reaction was conducted at room temperature. At 0 °C, the reaction gave a 3:1 mixture of 4 and 5, with 3 being formed in only minor amounts.
Source Title: Carbohydrate Letters
URI: http://scholarbank.nus.edu.sg/handle/10635/76473
ISSN: 10735070
Appears in Collections:Staff Publications

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