phenyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside | 179072-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside
• 英文别名: (2S,4aR,6S,7R,8R,8aS)-8-[(4-methoxyphenyl)methoxy]-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 179072-68-5
• 化学式: C₂₇H₂₈O₆S
• 分子量: 480.582
• InChiKey: HFWDGFHUHULTML-PJZCFIFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside 在 palladium on activated charcoal 吡啶 、 2,6-二甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 di-tert-butyl-4-methylpyridine 、 三氟甲磺酸酐 、 4 A molecular sieve 、 水 、 氢气 、 zinc trifluoromethanesulfonate 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 乙硫醇 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 37.58h， 生成 (2R,3R,4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,3R,4S,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-2-hydroxymethyl-4-methyl-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Total Synthesis of Everninomicin 13,384-1—Part 3: Synthesis of the DE Fragment and Completion of the Total Synthesis

  摘要：

  The stereoselective construction of the DE fragment (2) of everninomicin 13,384-1 (1) is reported. From the two possible ways of inserting the DE fragment between the A1B(A)C and FGHA2 domains of the natural product, the sequence involving the DEFGHA2 segment was found to be the most viable. This coupling was followed by attachment of a suitably protected and activated A1B(A)C fragment which led, after orthoester construction and final deprotection to the targeted everninomicin 13,384-1 (1), completing the total synthesis of this complex naturally occurring substance.

  DOI：

  10.1002/1521-3765(20000901)6:17<3149::aid-chem3149>3.0.co;2-l
• 作为产物：
  描述：

  苯基-1-硫醇-beta-D-半乳糖苷 在 camphor-10-sulfonic acid 、 二正丁基氧化锡 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 phenyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Orthogonal glycosylation strategy in synthesis of extended blood group B determinant

  摘要：

  The orthogonal glycosylation strategy was applied for the synthesis of extended blood type B determinant (2) of a novel glycolipid 1. Key features in the synthesis are 1) four monosaccharide units were synthesized as either glycosyl fluoride or thioglycoside to be engaged to the orthogonal glycosylation strategy and 2) all necessary manipulations were completed at the monosaccharide level, therefore, manipulations during the elongation of sugar chain were minimized. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00901-x

文献信息

• Synthesis of the Salmonella Type E₁ Core Trisaccharide as a Probe for the Generality of 1-(Benzenesulfinyl)piperidine/Triflic Anhydride Combination for Glycosidic Bond Formation from Thioglycosides
  作者：David Crich、Hongmei Li

  DOI：10.1021/jo0108818

  日期：2002.7.1

  A synthesis of a chromogenic glycoside of the Salmonella anatum group E-1 core trisaccharide is presented in which all three glycosidic bonds, a 1,2-cis-equatorial, a 1,2-trans-axial, and a 1,2-trans-equatorial linkage representing three of the four main classes of glycosidic bond, are formed with thioglycoside donors activated under a single set of conditions by the combination of 1-(benzenesulfinyl)piperidine and trifluoromethanesulfonic anhydride. 2,3-O-Carbonyl- and 2,3-O-isopropylidene-alpha-L-rhamnopyranosyI thioglycosides are found to be highly alpha-selective rhamnosyl donors under these conditions.
• Orthogonal glycosylation strategy in synthesis of extended blood group B determinant
  作者：Osamu Kanie、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/0040-4039(96)00901-x

  日期：1996.6

  The orthogonal glycosylation strategy was applied for the synthesis of extended blood type B determinant (2) of a novel glycolipid 1. Key features in the synthesis are 1) four monosaccharide units were synthesized as either glycosyl fluoride or thioglycoside to be engaged to the orthogonal glycosylation strategy and 2) all necessary manipulations were completed at the monosaccharide level, therefore, manipulations during the elongation of sugar chain were minimized. Copyright (C) 1996 Elsevier Science Ltd
• Total Synthesis of Everninomicin 13,384-1—Part 3: Synthesis of the DE Fragment and Completion of the Total Synthesis
  作者：K. C. Nicolaou、Helen J. Mitchell、Rosa Maria Rodríguez、Konstantina C. Fylaktakidou、Hideo Suzuki、Scott R. Conley

  DOI：10.1002/1521-3765(20000901)6:17<3149::aid-chem3149>3.0.co;2-l

  日期：2000.9.1

  The stereoselective construction of the DE fragment (2) of everninomicin 13,384-1 (1) is reported. From the two possible ways of inserting the DE fragment between the A1B(A)C and FGHA2 domains of the natural product, the sequence involving the DEFGHA2 segment was found to be the most viable. This coupling was followed by attachment of a suitably protected and activated A1B(A)C fragment which led, after orthoester construction and final deprotection to the targeted everninomicin 13,384-1 (1), completing the total synthesis of this complex naturally occurring substance.