octyl 2-acetamido-3-O-acetyl-2-deoxy-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside | 791834-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octyl 2-acetamido-3-O-acetyl-2-deoxy-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside
• 英文别名: TBDMS(-6)GlcNAc3Ac(b)-O-octyl；[(2R,3S,4R,5R,6R)-5-acetamido-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-6-octoxyoxan-4-yl] acetate
• CAS: 791834-88-3
• 化学式: C₂₄H₄₇NO₇Si
• 分子量: 489.725
• InChiKey: BJEXXARBAIQLQQ-GNJRFXKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  octyl 2-acetamido-3-O-acetyl-2-deoxy-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 30.0h， 生成 Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-3-((4aR,6S,7R,8S,8aS)-7,8-diacetoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-octyloxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Practical Synthesis of Sulfated Analogs of Lactosamine and Sialylated Lactosamine Derivatives

  摘要：

  A series Of beta-D-Gal-(1 --> 4)-beta-D-GlcNAc-octyl, NeuAcalpha-(2 --> 3)-beta-D-Gal-(1 --> 4)-beta-D-GlcNAc-octyl, and their 6-O-sulfated and 6'-O-sulfated analogs (1-6) were synthesized in a concise manner starting from readily accessible monosaccharide intermediates. The syntheses involved formation of an orthogonally protected disaccharide and a trisaccharide from which all six compounds were derived.

  DOI：

  10.1081/car-200030027
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 Acetic acid (2R,3R,4R,5S,6R)-3-acetylamino-5-hydroxy-6-hydroxymethyl-2-octyloxy-tetrahydro-pyran-4-yl ester 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以72%的产率得到octyl 2-acetamido-3-O-acetyl-2-deoxy-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside
  参考文献：
  名称：

  Practical Synthesis of Sulfated Analogs of Lactosamine and Sialylated Lactosamine Derivatives

  摘要：

  A series Of beta-D-Gal-(1 --> 4)-beta-D-GlcNAc-octyl, NeuAcalpha-(2 --> 3)-beta-D-Gal-(1 --> 4)-beta-D-GlcNAc-octyl, and their 6-O-sulfated and 6'-O-sulfated analogs (1-6) were synthesized in a concise manner starting from readily accessible monosaccharide intermediates. The syntheses involved formation of an orthogonally protected disaccharide and a trisaccharide from which all six compounds were derived.

  DOI：

  10.1081/car-200030027

文献信息

• Fluoridolysis of 5,6-epoxy carbohydrates: application to the synthesis of 5-fluoro lactosamine and isolactosamine glycosides
  作者：Tara L. Hagena、James K. Coward

  DOI：10.1016/j.tetasy.2009.03.025

  日期：2009.5

  The synthesis of 6-selenophenyl derivatives of β-1,3 and β-1,4 disaccharides has been explored for the purpose of extending our epoxide fluoridolysis methodology to the synthesis of 5-fluoro analogues of N-acetyl isolactosamine (isoLacNAc, lacto-N-biose) and N-acetyl lactosamine (LacNAc) glycosides. Successful synthesis of the C-6 selenium-containing disaccharides was achieved via Lewis acid-mediated

  为了将我们的环氧化物荧光分解方法扩展到N-乙酰基异乳糖胺（isoLacNAc，乳酸酯-）的5-氟类似物的合成，已经探索了β-1,3和β-1,4二糖的6-硒苯基衍生物的合成。N-二糖）和N-乙酰基乳糖胺（LacNAc）糖苷。通过路易斯酸介导的供体和受体底物成功合成了含C-6硒的二糖，后者含有选择性保护的C-6羟基，可最终转化为所需的6-硒代苯二糖。相反，在多种条件下使用含硒受体底物不能产生所需的含硒二糖。将6-硒代苯衍生物氧化为相应的亚硒酸盐，然后进行热消除，得到环外烯烃，其被转化为5，6-环氧化物。环氧氟化反应产生所需的目标化合物，即1型和2型聚糖的5-氟β-辛基糖苷类似物。