methyl 3,4-di-O-acetyl-2-O-trityl-α-L-rhamnopyranoside | 72398-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl 3,4-di-O-acetyl-2-O-trityl-α-L-rhamnopyranoside
• 英文别名: [(2S,3S,4R,5R,6R)-4-acetyloxy-6-methoxy-2-methyl-5-trityloxyoxan-3-yl] acetate
• CAS: 72398-21-1
• 化学式: C₃₀H₃₂O₇
• 分子量: 504.58
• InChiKey: HQOYOWSCRJVFCP-LMELKAPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4-Di-O-acetyl-1,2-O-(1-p-tolylthioethylidene)-β-L-rhamnopyranose 、 methyl 3,4-di-O-acetyl-2-O-trityl-α-L-rhamnopyranoside 在 triphenylmethyl perchlorate 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以64.5%的产率得到methyl 3,4-di-O-acetyl-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-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
• 作为产物：
  描述：

  methyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranoside 在 吡啶 、 2,4,6-三甲基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 1.42h， 生成 methyl 3,4-di-O-acetyl-2-O-trityl-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

文献信息

• Reactivity of sugar trityl ethers in trityl?cyanoalkylidene condensation
  作者：P. I. Kitov、Yu. E. Tsvetkov、L. V. Backinowsky、N. K. Kochetkov

  DOI：10.1007/bf00699016

  日期：1993.11

  The reactivity of a series of primary and secondary sugar trityl ethers in trityl-cyanoalkylidene condensation has been determined. It was found that the stereoselectivity of glycosylation by this method does not directly depend on the reactivity of the trityl ethers. Based on the results obtained, a stepwise mechanism rather than a concerted mechanism has been chosen as the most probable.
• Linear dependence of the glycosylation stereoselectivity ofO-trityl ethers by carbohydrate 1,2-O-cyanoalkylidene derivatives on anion concentrations. Effect of substituents in the glycosyl acceptor and a new mechanism of 1,2-cis-glycosides formation
  作者：P. I. Kitov、Yu. E. Tsvetkov、L. V. Backinowsky、N. K. Kochetkov

  DOI：10.1007/bf00707066

  日期：1995.6

  The dependence of the stereochemical outcome of trityl-cyanoalkylidene condensation (alpha/beta-ratio of disaccharides) on the concentration of a catalyst (TrClO(4)) was studied. The dependence was shown to be linear over a wide range of concentrations of the catalyst. The mechanism of the reaction and the effect of the nature of protective groups in the glycosyl acceptor on the stereochemistry of glycosylation are discussed. A new mechanism of 1,2-cis-glycosides formation is proposed.
• NIFANTEV, N. EH.;BAKINOVSKIJ, L. V.;KOCHETKOV, N. K., BIOORGAN. XIMIYA, 16,(1990) N0, S. 1402-1406
  作者：NIFANTEV, N. EH.、BAKINOVSKIJ, L. V.、KOCHETKOV, N. K.

  DOI：——

  日期：——