Jenkins I D, Goren M B
Chem Phys Lipids. 1986 Oct-Nov;41(3-4):225-35. doi: 10.1016/0009-3084(86)90024-1.
Treatment of trehalose with triphenylphosphine, diisopropyl azodicarboxylate and beta-O-tetrahydropyran-2-ylmycolic acid in 1:1 hexamethylphosphoric triamide/dichloromethane, followed by removal of the tetrahydropyranyl protecting group, gave cord factor (1) in good yield, under exceptionally mild conditions. Two new cord factor analogues were similarly prepared from beta-O-methylmycolic acid and from the alpha, beta-unsaturated 'anhydro' mycolic acid respectively. The procedure, employing excess trehalose, can also be used for the synthesis of trehalose monomycolates in good yield. No protection of the carbohydrate is required.
在1:1的六甲基磷酸三酰胺/二氯甲烷中，用三苯基膦、偶氮二羧酸二异丙酯和β -O-四氢吡喃-2-基霉菌酸处理海藻糖，然后除去四氢吡喃基保护基团，在异常温和的条件下，以良好的产率得到了索状因子（1）。分别从β -O-甲基霉菌酸和α,β-不饱和“脱水”霉菌酸类似地制备了两种新的索状因子类似物。该方法使用过量的海藻糖，也可用于高产率地合成海藻糖单霉菌酸酯。不需要对碳水化合物进行保护。
