DEBENZYLATION AND DETRITYLATION BY BROMODIMETHYLBORANE - SYNTHESIS OF MONO-ACID OR MIXED-ACID 1,2-DIACYL-SN-GLYCEROLS OR 2,3-DIACYL-SN-GLYCEROLS
DEBENZYLATION AND DETRITYLATION BY BROMODIMETHYLBORANE - SYNTHESIS OF MONO-ACID OR MIXED-ACID 1,2-DIACYL-SN-GLYCEROLS OR 2,3-DIACYL-SN-GLYCEROLS
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DOI：
10.1016/0009-3084(92)90009-e
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发表时间：
1992-04-01
影响因子：
3.4
通讯作者：
DUCLOS, RI
中科院分区：
文献类型：
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作者：
KODALI, DR;DUCLOS, RI
用溴代甲基硼烷在温和的反应条件下(二氯甲烷，-20~5-C)脱保护了由苄基或三丁基保护的伯醇，用于合成光学纯的一酸或混合酸1，2-或2，3-二酰基-sn-甘油。该方法特别适用于长饱和酰基(C12至C24)以及不饱和二酰基-sn-甘油的合成，因为在脱保护过程中很少或没有发生酰基迁移。3-苄基-n-甘油或1-苄基-n-甘油经二酰化反应，再经溴甲基硼烷脱苄反应，分别得到单酸1，2-或2，3-二酰基-n-甘油。以1-酰基-n-甘油或3-酰基-n-甘油为原料，分别经三酰化、与不同脂肪酸的酰化、再与溴代甲基硼烷去三酰化反应制得混酸1，2-或2，3-二酰基-n-甘油。
A novel method of deprotecting primary alcohols protected with either benzyl or trityl groups by using bromodimethylborane under mild reaction conditions (dichloromethane, -20 to 5-degrees-C) has been applied to the synthesis of optically pure mono-acid or mixed acid 1,2- or 2,3-diacyl-sn-glycerols. This method was particularly useful for the synthesis of long saturated acyl (C12 to C24) as well as unsaturated diacyl-sn-glycerols since little or no acyl migration occurred during deprotection. Diacylation of 3-benzyl-sn-glycerol or 1-benzyl-sn-glycerol followed by bromodimethylborane debenzylation gave mono-acid 1,2- or 2,3-diacyl-sn-glycerols, respectively. The mixed-acid 1,2- or 2,3-diacyl-sn-glycerols were prepared from 1-acyl-sn-glycerols or 3-acyl-sn-glycerols, respectively, by tritylation, acylation with a different fatty acid, followed by detritylation with bromodimethylborane.