2-isobutenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 15890-75-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-isobutenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: tetraacetyl methallyl β-glucoside；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(2-methylprop-2-enoxy)oxan-2-yl]methyl acetate
• CAS: 15890-75-2
• 化学式: C₁₈H₂₆O₁₀
• 分子量: 402.398
• InChiKey: YRYFUTOYQOMACS-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-isobutenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 二甲基硫 、 sodium hydride 、 potassium carbonate 、 臭氧 作用下， 以 甲醇 为溶剂， 反应 1.25h， 生成 osmaronin
  参考文献：
  名称：

  Chemoenzymatic syntheses of naturally occurring β-glucosides

  摘要：

  Enzymatic glycosidation of the various kinds of primary alcohols 5, 7, 9, 11, 13 and 15 and 4-nitrophenyl-beta-D-glucopyranoside 4 using beta-glucosidase from almonds gave stereoselectively beta-D-glucosides 6, 8, 10, 12, 14 and 16 including the naturally occurring beta-glucosides in moderate yield. Among them, the beta-glucosides 6, 8 and 10 were converted to the cyanoglycosides, rhodiocyanoside A 20a, osmaronin 24a and sutherlandin 29, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00228-1
• 作为产物：
  描述：

  4-硝基苯-Β-D-吡喃葡萄糖苷 在 吡啶 、 4-二甲氨基吡啶 、 phosphate buffer 、 β-glucosidase 作用下， 反应 5.0h， 生成 2-isobutenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic syntheses of naturally occurring β-glucosides

  摘要：

  Enzymatic glycosidation of the various kinds of primary alcohols 5, 7, 9, 11, 13 and 15 and 4-nitrophenyl-beta-D-glucopyranoside 4 using beta-glucosidase from almonds gave stereoselectively beta-D-glucosides 6, 8, 10, 12, 14 and 16 including the naturally occurring beta-glucosides in moderate yield. Among them, the beta-glucosides 6, 8 and 10 were converted to the cyanoglycosides, rhodiocyanoside A 20a, osmaronin 24a and sutherlandin 29, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00228-1

文献信息

• Stereoselective Dihydroxylation Reaction of Alkenyl β-D-Hexopyranosides: A Methodology for the Synthesis of Glycosylglycerol Derivatives and 1-O-Acyl-3-O-β-D-glycosyl-sn-glycerol Analogues
  作者：José M. Vega-Pérez、Carlos Palo-Nieto、Ignacio Periñán、Margarita Vega-Holm、José M. Calderón-Montaño、Miguel López-Lázaro、Fernando Iglesias-Guerra

  DOI：10.1002/ejoc.201101539

  日期：2012.2

  A variety of new glycosylglycerol derivatives have been prepared by stereoselective dihydroxylation of a range of alkenyl β-D-hexopyanosides under Donohoe's conditions. We have studied the relationship between the diastereoisomeric excess and the structural features of the precursor (sugar and alkenyl moieties). The stereochemical yields demonstrated that the presence of a hydrogen-bond donor group

  在 Donohoe 条件下，通过一系列烯基 β-D-己酮苷的立体选择性二羟基化，制备了多种新的糖基甘油衍生物。我们研究了非对映异构体过量与前体（糖和烯基部分）的结构特征之间的关系。立体化学产率表明糖部分的 2 位存在氢键供体基团 (OH, NHAc) 是获得高水平立体识别力所必需的。新的 1-O-酰基-3-O-β-D-糖基-sn-甘油类似物是通过用脂肪酸对伯羟基进行官能化而获得的。还提供了糖基甘油和糖基甘油脂类似物的初步细胞毒活性分析。
• Catalytic osmylation of allyl D-glucopyranoside
  作者：M.K. Gurjar、Anupama S Mainkar

  DOI：10.1016/s0957-4166(00)82306-x

  日期：1992.1

  Catalytic osmylation of allyl D-glucopyranoside leading to the formation of glycosyl glycerol derivatives is described.
• Synthesis and immunological evaluation of the 4-β-glucoside of HMBPP
  作者：José-Luis Giner、Hong Wang、Craig T. Morita

  DOI：10.1016/j.bmcl.2011.12.055

  日期：2012.1

  HMBPP ((E)-4-hydroxy-3-methyl-2-butenyl pyrophosphate) is a highly potent innate immunogen that stimulates human gamma delta T cells expressing the V gamma 2V delta 2 T cell antigen receptor. To determine if glycoside conjugates of HMBPP retain activity, the 4-beta-glucoside and its acetylated homolog were synthesized and tested for their ability to stimulate gamma delta T cells. The glycoside HMBPP conjugate stimulated human gamma delta T cells with an EC50 of 78 nM. The tetraacetyl glycoside HMBPP conjugate was also active (EC50 = 360 nM). The two isomeric mono-beta-glucosides of the parent (E)-2-methylbut-2-ene-1,4-diol, however, were not active. Thus, HMBPP glycosylated at the 4-OH position stimulates gamma delta T cells as long as the pyrophosphate moiety is present. (C) 2011 Elsevier Ltd. All rights reserved.