β-methyl-2,3-di-O-acetyl-4-O-trityl-D-xylopyranoside | 88306-51-8

• 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: β-methyl-2,3-di-O-acetyl-4-O-trityl-D-xylopyranoside
• 英文别名: 4-O-trityl-2,3-di-O-acetyl-β-methyl-D-xylopyranoside；methyl 2,3-di-O-acetyl-4-O-trityl-β-D-xylopyranoside；methyl-2,3-di-O-acetyl-4-O-trityl-β-D-xylopyranoside；[(2R,3R,4S,5R)-3-acetyloxy-2-methoxy-5-trityloxyoxan-4-yl] acetate
• CAS: 88306-51-8
• 化学式: C₂₉H₃₀O₇
• 分子量: 490.553
• InChiKey: AKQXFUMMSIIXDI-JUDWXZBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  β-methyl-2,3-di-O-acetyl-4-O-trityl-D-xylopyranoside 在 triphenylmethyl perchlorate 作用下， 以 二氯甲烷 为溶剂， 生成 methyl-O-(2,3,4-tri-O-acetyl-α-D-xylopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  Glycosylation of methyl-2,3-di-O-acetyl-?-D-xylopyranoside triarylmethyl ethers with electron-donor substituents in the aromatic ring by 3,4-di-O-acetyl-1,2-O-[1-(endo-cyano)-ethylidene]-?-D-xylo-pyranose

  摘要：

  DOI：

  10.1007/bf00962335
• 作为产物：
  描述：

  methyl 2,3-di-O-acetyl-β-D-xylopyranoside 在 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 17.33h， 生成 β-methyl-2,3-di-O-acetyl-4-O-trityl-D-xylopyranoside
  参考文献：
  名称：

  Glycosylation of methyl-2,3-di-O-acetyl-?-D-xylopyranoside triarylmethyl ethers with electron-donor substituents in the aromatic ring by 3,4-di-O-acetyl-1,2-O-[1-(endo-cyano)-ethylidene]-?-D-xylo-pyranose

  摘要：

  DOI：

  10.1007/bf00962335

文献信息

• The effect of replacing a 3-O-acetyl group by a 3-O-benzyl group in a methyl 4-O-trityl-β-d-xylopyranoside derivative on the efficiency of 1,2-trans-glycosylation with a d-xylose 1,2-O-(1-cyanoethylidene) derivative
  作者：Nikolay E. Nifant'ev、Leon V. Backinowsky、Nikolay K. Kochetkov

  DOI：10.1016/0008-6215(89)85042-6

  日期：1989.8

  Abstract Replacement of AcO-3 in methyl 2,3-di- O -acetyl-4- O -trityl-β- d -xylopyranoside with a benzyl group greatly increases the 1,2- trans -stereoselectivity of glycosylation with a d -xylopyranose 1,2- O -(1-cyanoethylidene) derivative. Anomerisation of methyl 2- O -benzyl-β- d -xylopyranoside derivatives occurred under the action of triphenylmethylium perchlorate.

  摘要用苄基取代2，3-二-O-乙酰基-4-O-三苯甲基-β-d-吡喃吡喃糖苷中的AcO-3大大提高了ad-吡喃吡喃糖1糖基化反应的1,2-反式-立体选择性。 ，2-O-（1-氰基亚乙基）衍生物。在高氯酸三苯基甲酯的作用下，甲基2-O-苄基-β-d-吡喃吡喃糖苷衍生物发生了异构化。
• The effect of high pressure on the stereospecificity of the glycosylation reaction
  作者：Nikolay K. Kochetkov、Victor M. Zhulin、Evgeny M. Klimov、Nelly N. Malysheva、Zinaida G. Makarova、Andrej Ya. Ott

  DOI：10.1016/0008-6215(87)80133-7

  日期：1987.7

  a pressure of 1.4 GPa and room temperature, the glycosylation of trityl ethers by 1,2-O-cyanoethylidene derivatives of sugars, and the polycondensation of the proper monomers in dichloromethane, proceed with absolute stereospecificity, giving rise to a 1,2-trans-glycosidic linkage, although, at the ambient pressure, the reactions studied reveal a rather low stereospecificity. The effect of high pressure

  在1.4 GPa的压力和室温下，糖的1,2-O-氰基亚乙基衍生物对三苯甲基醚的糖基化作用以及适当单体在二氯甲烷中的缩聚反应具有绝对立体定向性，从而产生1,2-反式糖苷键，尽管在环境压力下，所研究的反应显示出较低的立体特异性。高压对糖苷键形成的立体特异性的影响被解释为是由于随着压力的增加，单环糖基阳离子和双环酰基氧鎓阳离子之间的平衡向后者转移。
• 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.
• Zhulin, V. M.; Klimov, E. M.; Makarov, Z. G., Doklady Chemistry, 1986, vol. 289, p. 245 - 247
  作者：Zhulin, V. M.、Klimov, E. M.、Makarov, Z. G.、Malysheva, N. N.、Kochetkov, N. K.

  DOI：——

  日期：——
• 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.