methyl 2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside | 90164-72-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
• CAS: 90164-72-0
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: YZRYSXUUTNFSCL-CYKOTILYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 在 silver trifluoromethanesulfonate 2,4,6-三甲基吡啶 、 三氟甲磺酸 、 sodium 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 环己烷 为溶剂， 反应 72.0h， 生成 methyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-4-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Wessel, Hans-Peter; Bundle, David R., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2251 - 2260

  摘要：

  DOI：
• 作为产物：
  描述：

  triphenylcarbenium tetrafluoroborate 、 (2,3R,S)-4-O-benzyl-2,3-O-benzylidene α-L-rhamnopyranoside 以 乙腈 为溶剂， 以75%的产率得到methyl 2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Wessel, Hans-Peter; Bundle, David R., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2251 - 2260

  摘要：

  DOI：

文献信息

• Synthesis of a Tri- and Tetrasaccharide Fragment Specific for the <i>Shigella flexneri</i> Serotype 5a <i>O</i>-Antigen. A Reinvestigation
  作者：Laurence A. Mulard、Joël Ughetto-Monfrin

  DOI：10.1080/07328309908544033

  日期：1999.1.1

  Stereocontrolled, stepwise synthesis of methyl α-L-rhamnopyranosyl-(1→2)-[α-D-glucopyranosyl-(1→3)]-α-L-rhamnopyranoside (A(E)B, 1) and methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→2)-[α-D-glucopyranosyl-(1→3)]-α-L-rhamnopyranoside (DA(E)B, 2) is described; these constitute the methyl glycosides of fragments of the O-specific polysaccharide of Shigella flexneri serotype

  立体控制逐步合成甲基α-L-鼠李吡喃糖苷-（1→2）-[α-D-吡喃葡萄糖基-（1→3）]-α-L-鼠李吡喃糖苷（A（E）B，1）和甲基2-乙酰氨基-2-脱氧-β-D-吡喃吡喃糖基-（1→2）-α-L-鼠李吡喃糖基-（1→2）-[α-D-吡喃吡喃糖基-（1→3）]-α-L-鼠李糖吡喃糖苷（描述了DA（E）B，2）；这些构成了志贺氏志贺氏菌血清型5a的O-特异性多糖的片段的甲基糖苷。考虑了三糖1的两种途径。路线1涉及前体与残基A和二糖EB的偶联，而路线2基于前体与残基E和二糖的缩合。AB。出乎意料的是，后者提供了1的β-异头物，即甲基α-L-鼠李吡喃糖基-（1→2）-[β-D-吡喃吡喃糖基-（1→3）]-α-L-鼠李糖吡喃糖苷。 。首选路线1。总体而言，在这项研究中进行的一些观察表明，为了构建更高的片段，鼠李糖A的合适前体将需要在位置3和4处具有低膨松度的保护基团。因此，2- O-乙酰基3,
• Synthesis and two-dimensional nuclear magnetic resonance analysis of a tetra- and a hexa-saccharide fragment of the O-specific polysaccharide of Shigella dysenteriae type 1
  作者：Vince Pozsgay、Bruce Coxon

  DOI：10.1016/0008-6215(94)80035-9

  日期：1994.5

  The synthesis of the tetra- and hexa-saccharide methyl glycosides alpha-D-Galp-(1-->3)-alpha-D-GlcpNAc-(1-->3)-alpha-L-Rhap-(1-->3)- alpha-L-Rhap- OMe (1), and alpha-L-Rhap-(1-->3)-alpha-L-Rhap-(1-->2)-alpha-D-Galp-(1--> 3)-alpha-D-GlcpNAc- (1-->3)-alpha-L-Rhap-(1-->3)-alpha-L-Rhap-OMe (3) is described, which represent various epitopes of the O-specific polysaccharide of Shigella dysenteriae type 1.

  6-四-O-苄基-1-硫代-β-D-吡喃半乳糖苷（16）和2-叠氮基-4,6-O-亚苄基-3-O-溴乙酰基-2-脱氧-β-D-吡喃葡萄糖基氯（19）。对寡糖1和3的1H和13C NMR光谱进行的详细分析证实，六糖3比1或同源五糖41更好地接近天然多糖的构象。
• Novel glycosidation methodology. The use of phenyl selenoglycosides as glycosyl donors and acceptors in oligosaccharide synthesis
  作者：Seema Mehta、B. Mario Pinto

  DOI：10.1021/jo00064a012

  日期：1993.6

  The use of phenyl selenoglycosides as glycosyl donors and acceptors in glycosidation reactions is described. The versatility of these novel compounds is illustrated by the selective activation of both ''disarmed'' and ''armed'' phenyl selenoglycoside donors over ''armed'' ethyl thioglycoside acceptors with silver trifluoromethanesulfonate in the presence of potassium or silver carbonate to give disaccharides in excellent yield. Selective activation of glycosyl bromide donors over phenyl selenoglycoside acceptors is realized by silver trifluoromethanesulfonate promotion in the presence of collidine. Such selectivity is also demonstrated by the activation of a glycosyl trichloroacetimidate donor in the presence of selenoglycoside acceptors with triethylsilyl trifluoromethanesulfonate. The central role of selenoglycosides is illustrated by the synthesis of a trisaccharide that profits from the sequential, selective activation of a glycosyl bromide donor over a selenoglycoside acceptor and the resulting disaccharide selenoglycoside over a thioglycoside acceptor. The liberation of the anomeric hydroxyl group from a phenyl selenoglycoside is also described.