IODONIUM ION-MEDIATED MANNOSYLATIONS OF MYOINOSITOL - SYNTHESIS OF A MYCOBACTERIA PHOSPHOLIPID FRAGMENT
IODONIUM ION-MEDIATED MANNOSYLATIONS OF MYOINOSITOL - SYNTHESIS OF A MYCOBACTERIA PHOSPHOLIPID FRAGMENT
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DOI：
10.1080/07328309208020088
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发表时间：
1992-01-01
影响因子：
1
通讯作者：
VANBOOM, JH
中科院分区：
文献类型：
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作者：
ELIE, CJJ;VERDUYN, R;VANBOOM, JH
碘鎓离子介导的 1-O-烯丙基-3,4,5-三-O-苯甲基-6-O-对-甲氧基苯甲基-D/L-肌醇与乙基 2-O-苯甲酰基-3,4,6-三-O-苯甲基-l-硫代-α-D-吡喃甘露糖苷的糖基化在去除 对甲氧基苄基和柱色谱，单个非对映异构二糖的α/β-混合物。随后通过相同的乙基1-吡喃硫代甘露糖苷供体对α(1-2)连接的吡喃甘露糖基-D-肌醇对映体进行立体特异性糖基化，在去苯甲酰化、苄基化和随后的去烯丙基化之后，提供部分苄基化的2，6-二甘露吡喃糖基-D-肌醇衍生物， 通过H-膦酸酯法，用1,2-二棕榈酰-sn-甘油将其HO-1位置磷酸化。中间体膦酸二酯的氧化，以及随后的O-苄基的氢解，得到目标化合物1-O-(1,2-二棕榈酰基-sn-甘油-3-磷酰基)-2,6-二-O-α-D-吡喃甘露糖基-D-肌醇。
Iodonium ion-mediated glycosylation of 1-O-allyl-3,4,5-tri-O-benzyl-6-O-para-methoxybenzyl-D/L-myo-inositol by ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-l-thio-alpha-D-mannopyranoside gave, after removal of the para-methoxybenzyl group and column chromatography, an alpha/beta-mixture of the individual diastereoisomeric disaccharides. Subsequent stereospecific glycosylation of the alpha(1-2) linked mannopyranosyl-D-myo-inositol enantiomorph by the same ethyl 1 -thiomannopyranoside donor afforded, after debenzoylation, benzylation and subsequent deallylation the partially benzylated 2,6-dimannopyranosyl-D-myo-inositol derivative, the HO-1 position of which was phosphorylated, via the H-phosphonate method, with 1,2-dipalmitoyl-sn-glycerol. Oxidation of the intermediate phosphonate diester, and subsequent hydrogenolysis of the O-benzyl groups, furnished the target compound 1-O-(1,2-dipalmitoyl-sn-glycero-3-phosphoryl)-2,6-di-O-alpha-D-mannopyranosyl-D-myo-inositol.