allyl 2,4,6-tri-O-acetyl-3-O-methyl-β-D-glucopyranoside | 129192-93-4

• 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: allyl 2,4,6-tri-O-acetyl-3-O-methyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,5-diacetyloxy-4-methoxy-6-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 129192-93-4
• 化学式: C₁₆H₂₄O₉
• 分子量: 360.361
• InChiKey: FXHDMUDXVLFCLH-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  allyl 2,4,6-tri-O-acetyl-3-O-methyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以86%的产率得到allyl 3-O-methyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of allyl glycosides for conversion into neoglycoproteins bearing epitopes of mycobacterial glycolipid antigens

  摘要：

  Neoglycoproteins bearing key glycosyl substituents of several glycopeptidolipid antigens of pathogenic Mycobacterium species have been synthesized. Allyl glycosides of the terminal 6-deoxyhexose-containing units of the antigens were prepared, with appropriate ether and ester substituents in place. Ozonolysis of the allyl glycosides was then followed by reductive coupling with epsilon-amino groups of lysine residues in bovine serum albumin, using sodium cyanoborohydride at pH 7.8. The resulting neoglycoproteins emulated the antigenicity of the native molecule in several serological tests.

  DOI：

  10.1016/0008-6215(92)84172-o
• 作为产物：
  描述：

  1,2,4,6-tetra-O-acetyl-3-O-methyl-β-D-glucopyranose 在 4 A molecular sieve 、 三氟化硼乙醚 、 乙酸肼 、 1,5-Diazabicyclo[5.4.0]undec-5-ene 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 生成 allyl 2,4,6-tri-O-acetyl-3-O-methyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of allyl glycosides for conversion into neoglycoproteins bearing epitopes of mycobacterial glycolipid antigens

  摘要：

  Neoglycoproteins bearing key glycosyl substituents of several glycopeptidolipid antigens of pathogenic Mycobacterium species have been synthesized. Allyl glycosides of the terminal 6-deoxyhexose-containing units of the antigens were prepared, with appropriate ether and ester substituents in place. Ozonolysis of the allyl glycosides was then followed by reductive coupling with epsilon-amino groups of lysine residues in bovine serum albumin, using sodium cyanoborohydride at pH 7.8. The resulting neoglycoproteins emulated the antigenicity of the native molecule in several serological tests.

  DOI：

  10.1016/0008-6215(92)84172-o

文献信息

• New modified single chained glycolipids. Part 1: synthesis of deoxy and partially O-methylated glycolipids with or without a sulfur containing spacer
  作者：M Schmidt、S.K Chatterjee、B Dobner、P Nuhn

  DOI：10.1016/s0009-3084(01)00196-7

  日期：2002.2

  Beside the differences in the configuration between unfunctionalized glycopyranoses like D-glucose, D-galactose and D-mannose, a number of deoxy and partially O-methylated sugar derivatives was prepared. The divergences concerning the different carbohydrate headgroups and the hydrophobic moiety, respectively, can be compared to relatively simple structured glycolipids with hexadecyl residue and without spacer

  描述了一种以高产率和端基异构体纯度合成新糖脂的方法。合成策略的起点是具有确定的空间取向的烯丙醇的糖基化。通过光加成正十六烷硫醇和3-巯基丙酸，然后分别用正十六烷基胺酰胺化，可以实现疏水部分的引入。为了研究不同糖基团对普通糖脂的理化行为，特别是烷基链的取向的影响，合成了一系列新糖脂。除了未官能化的吡喃葡萄糖如D-葡萄糖，D-半乳糖和D-甘露糖之间的构型差异之外，还制备了许多脱氧和部分O-甲基化的糖衍生物。
• A stereoselective synthesis of pyruvic 4,6-acetals of d-hexopyranose residues
  作者：Gerald O. Aspinall、Ibrahim H. Ibrahim、Naveen K. Khare

  DOI：10.1016/0008-6215(90)84195-z

  日期：1990.4

  Abstract A stereoselective synthesis of pyruvic 4,6-acetals in their naturally occurring configurations on α- d -glucopyranose, α- d -mannopyranose, and β- d -galactopyranose residues is based on the preferential formation of 4,6-[1-(3,4-dimethoxyphenyl)ethylidene] acetals bearing equatorial methyl groups. 2,3-Di- O -acyl derivatives of these acetals are oxidized with ruthenium tetraoxide to yield

  摘要立体选择性合成丙酮酸4,6-乙缩醛在α-d-吡喃葡萄糖，α-d-甘露吡喃糖和β-d-吡喃半乳糖上的残留是基于4,6- [1-带有赤道甲基的（3，4-二甲氧基苯基）亚乙基]缩醛。用四氧化钌氧化这些缩醛的2，3-二-O-酰基衍生物，得到相应的4，6-（1-羧乙叉基）缩醛。已经实现了烯丙基4，6-O [1（S）-1-甲氧基羰基亚乙基] -3-O-甲基-β-d-吡喃葡萄糖苷的合成，并通过环氧化保护烯丙基糖苷，随后用3-甲基苯并噻唑-进行再生脱氧。 2-硒。烯丙基糖苷已按顺序进行了皂化，臭氧分解，
• ASPINALL, GERALD O.;IBRAHIM, IBRAHIM H.;KHARE, NAVEEN K., CARBOHYDR. RES., 200,(1990) C. 247-256
  作者：ASPINALL, GERALD O.、IBRAHIM, IBRAHIM H.、KHARE, NAVEEN K.

  DOI：——

  日期：——