Prodrugs of vitamin C: the reaction of 1-acyloxyalkyl-1-iodides with vitamin C 5,6-acetonide

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• 作者：Jennifer McGowan ; Nikki Thiele ; Kenneth B. Sloan ; ^{sloan@cop.ufl.edu" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Vitamin C ; Vitamin C 5 ; 6-acetonide ; Prodrugs ; O-alkylation ; Soft alkyl derivatives
• 刊名：Tetrahedron Letters
• 出版年：2015
• 出版时间：30 September 2015
• 年：2015
• 卷：56
• 期：40
• 页码：5441-5444
• 全文大小：482 K

文摘

The reaction of 2 equiv of 1-acyloxyalkyl-1-iodides with vitamin C 5,6-acetonide gave mixtures of products that were O-alkylated on the 3-position and either O-alkylated, class="boldFont">7, or O-acylated, class="boldFont">8, on the 2-position. The class="boldFont">8 products comprised the majority of the mixtures: 56:54 to 94:6. The 3-alkylated-2-acylated prodrugs, class="boldFont">8, hydrolyzed to vitamin C 5,6-acetonide chemically at pH 7.4 with half-lives of 6–12 h.