d-fructose derivatives modified at C-4 by direct displacementand by oxirane opening
作者:R.D. Guthrie、Ian D. Jenkins、San Thang、James J. Watters、Ryohei Yamasaki
DOI:10.1016/s0008-6215(82)80002-5
日期:1982.5
Abstract The epoxide ring of methyl 3,4-anhydro- β - d -tagatofuranoside is opened byattack of nucleophiles at C-4 to yield derivatives of D-fructose. Treatment of 2,3- O -isopropylidene-1,6-di- Op -tolylsulfonyl- β - d -fructofuranose with sulfuryl chloride resulted in attack at C-6, not C-4. 2,3- O -Isopropylidene-1,6-di- O - p -tolylsulfonyl- β - d -tagatofuranose behaved normally with this reagent
摘要3,4-脱水-β-d-塔古呋喃糖苷甲基的环氧化物是通过亲核试剂在C-4处打开而生成D-果糖的衍生物。用磺酰氯处理2,3-O-异亚丙基-1,6-二-O-甲苯基磺酰基-β-d-果糖呋喃糖导致在C-6而不是C-4的进攻。2,3-O-异亚丙基-1,6-di-O-对甲苯磺酰基-β-d-塔呋喃呋喃糖的行为正常。转化酶不水解4-脱氧-β-d-苏-呋喃呋喃糖苷甲基。