methyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside | 39687-43-9

• 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: methyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside
• 英文别名: methyl 4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside；[(2R,3R,4S,5R,6S)-6-[[(3aR,4R,6S,7S,7aR)-4-methoxy-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 39687-43-9
• 化学式: C₂₄H₃₆O₁₄
• 分子量: 548.541
• InChiKey: BMMDYMXTKYQOJD-WMYYQLBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以100%的产率得到methyl 4-O-β-D-glucopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
  参考文献：
  名称：

  与55型克雷伯菌的抗原重复单元有关的四糖的合成。

  摘要：

  DOI：

  10.1016/0008-6215(94)80077-4
• 作为产物：
  描述：

  甲基 2,3-O-异亚丙基-alpha-L-吡喃鼠李糖苷 在 triphenylmethyl perchlorate 2,6-二甲基吡啶 、 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of 1,2-trans-disaccharides via sugar thio-orthoesters

  摘要：

  DOI：

  10.1016/s0008-6215(00)84672-8
• 作为试剂：
  描述：

  3,4,6-tri-O-acetyl-1,2-O-(exo-cyanethylidene)-β-D-mannopyranose 、 methyl 2,3-O-isopropylidene-4-O-trityl-α-L-rhamnopyranoside 、 3,5,6-tri-O-acetyl-1,2-O-<(1-exo-cyano)ethylidene>-α-D-galactofuranose 在 methyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside 、 D-山梨糖醇六乙酸酯 、 Cl⁽³⁾HO₄ 作用下， 以 二氯甲烷 为溶剂， 生成 2,2,2-三苯基乙腈 、 methyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-L-rhamnopyranoside 、 methyl 2,3-O-isopropylidene-4-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Reactivity of 1,2-O-cyanoalkylidene sugar derivatives in trityl-cyanoalkylidene condensation

  摘要：

  The rate-determining step of trityl-cyanoalkylidene condensation is the interaction between the cyanoalkylidene derivative (CD) and the triphenylmethyl cation. The rate of the reaction follows first-order kinetics with respect to both CD and the catalyst (Tr+) and is independent of the nature and concentration of the trityl ether. Glycosylation rate constants have been determined for CD's of most common monosaccharides.

  DOI：

  10.1007/bf00699947

文献信息

• Amberlyst 15 as a mild and effective activator for the glycosylation with disarmed glycosyl trichloroacetimidate donors
  作者：Qiang Tian、Shuo Zhang、Qian Yu、Mei-Bo He、Jin-Song Yang

  DOI：10.1016/j.tet.2006.12.091

  日期：2007.3

  Amberlyst 15 acidic resin has been shown to be a mild and effective activator for the glycosylation with commonly used disarmed glycosyl trichloroacetimidate donors. Glucosylation, galactosylation, rhamnosylation, and lactosylation of a panel of representative alcohol and thiol acceptors promoted by Amberlyst 15 allowed for the formation of structurally diverse O- or S-linked oligosaccharides and glycosylated

  Amberlyst 15酸性树脂已被证明是一种温和有效的活化剂，可用于与常用的脱甲糖基三氯乙酰亚氨酸酯供体进行糖基化反应。由Amberlyst 15促进的一组代表性醇和硫醇受体的糖基化，半乳糖基化，鼠李糖基化和乳糖基化可以中等至极好的产率形成结构多样的O或S联寡糖和糖基化氨基酸。
• Collins, Peter M.; Munasinghe, V. Ranjit N., Journal of the Chemical Society. Perkin transactions I, 1983, # 8, p. 1879 - 1884
  作者：Collins, Peter M.、Munasinghe, V. Ranjit N.

  DOI：——

  日期：——
• Synthesis of a tetrasaccharide related to the repeating unit of the antigen from Klebsiella type 55
  作者：Saibal Kumar Das、Rina Ghosh、Asim Kumar Ray、Nirmolendu Roy

  DOI：10.1016/0008-6215(94)80077-4

  日期：1994.2
• Synthesis of 1,2-trans-disaccharides via sugar thio-orthoesters
  作者：Leon V. Backinowsky、Yury E. Tsvetkov、Nikolay F. Balan、Narguiz E. Byramova、Nikolay K. Kochetkov

  DOI：10.1016/s0008-6215(00)84672-8

  日期：1980.10
• Reactivity of 1,2-O-cyanoalkylidene sugar derivatives in trityl-cyanoalkylidene condensation
  作者：P. I. Kitov、Yu. E. Tsvetkov、L. V. Backinowsky、N. K. Kochetkov

  DOI：10.1007/bf00699947

  日期：1993.8

  The rate-determining step of trityl-cyanoalkylidene condensation is the interaction between the cyanoalkylidene derivative (CD) and the triphenylmethyl cation. The rate of the reaction follows first-order kinetics with respect to both CD and the catalyst (Tr+) and is independent of the nature and concentration of the trityl ether. Glycosylation rate constants have been determined for CD's of most common monosaccharides.