methyl 2,3-O-isopropylidene-4-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-α-L-rhamnopyranoside | 97321-42-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-O-isopropylidene-4-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-α-L-rhamnopyranoside
• 英文别名: methyl 4-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside；[(2R)-2-[(2S,3S,4R,5R)-5-[[(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-diacetyloxyoxolan-2-yl]-2-acetyloxyethyl] acetate
• CAS: 97321-42-1
• 化学式: C₂₄H₃₆O₁₄
• 分子量: 548.541
• InChiKey: MPGLDSLUQTXAEV-ILQPYPPCSA-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：
  13
• 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

• 作为产物：
  描述：

  乙酸酐 、 (2R,3S,4S,5R,6S)-6-Ethylsulfanyl-6-((3aR,4R,6S,7S,7aR)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-hexane-1,2,3,4,5-pentaol 在 4-二甲氨基吡啶 、 mercury dichloride 、 mercury(II) oxide 作用下， 生成 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：

  Use of Acyclic Glycosyl Donors for Furanoside Synthesis

  摘要：

  Treatment of the peracetylated ethyl dithioacetals of D-glucose, D-galactose, and D-mannose with acetyl chloride and boron trifluoride diethyl etherate at reflux yields the known acyclic 1-chlorol-(ethylthio) derivatives. These compounds are shown to effectively glycosylate a variety of carbohydrate accepters using silver trifluoromethanesulfonate as the promotor, affording stereospecifically the corresponding acyclic O,S-acetals in good to excellent yield. Furthermore, following deacetylation, treatment of these O,S-acetals with a mixture of mercuric salts in either methanol or dimethylformamide gives rise to disaccharides terminating in D-furanosyl residues.

  DOI：

  10.1021/jo9618583

文献信息

• 1,2-O-cyanoalkylidene derivatives of furanoses as 1,2-trans-glycosylating agents
  作者：Leon V. Backinowsky、Sergei A. Nepogod'ev、Alexander S. Shashkov、Nikolay K. Kochetkov

  DOI：10.1016/0008-6215(85)85221-6

  日期：1985.4

  with trimethylsilyl cyanide in acetonitrile in the presence of stannous chloride gave the respective 1,2-O-(1-cyanoethylidene) derivatives. Triphenyl-methylium perchlorate-catalysed glycosylation of trityl ethers of monosaccharides by the above cyanoethylidene derivatives and by 3,5-di-O-benzoyl-1,2-O-(α-cyanobenzylidene)-β-l-arabinofuranose gave high yields of protected disaccharides containing a

  在氯化亚锡存在下，在乙腈中用三甲基甲硅烷基氰化物处理乙酰化的1-阿拉伯呋喃糖，d-半乳糖呋喃糖和d-葡萄糖呋喃糖，分别得到1,2-O-（1-氰基亚乙基）衍生物。上述氰基亚乙基衍生物和3,5-二-O-苯甲酰基-1,2-O-（α-氰基苄叉基）-β-1-阿拉伯呋喃糖的三苯基甲基高氯酸盐催化的单糖三苯甲基醚的糖基化反应产生了高收率的被保护的含有1，2-反式-呋喃糖苷键的二糖。
• 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.