methyl 2,3-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-xylopyranoside | 88299-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-xylopyranoside
• 英文别名: Gal2Ac3Ac4Ac6Ac(a1-4)b-Xyl1Me2Ac3Ac；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(3R,4S,5R,6R)-4,5-diacetyloxy-6-methoxyoxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 88299-98-3
• 化学式: C₂₄H₃₄O₁₆
• 分子量: 578.524
• InChiKey: GYWMPRKNEQSIOQ-MQBLNODSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  195
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-1,2-O-<1-(endo-cyano)-ethylidene>-α-D-galactopyranose 、 β-methyl-2,3-di-O-acetyl-4-O-trityl-D-xylopyranoside 在 Cl⁽³⁾HO₄ 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl 2,3-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-xylopyranoside 、 methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1007/bf00707066

文献信息

• Studies of the molecular recognition of synthetic methyl β-lactoside analogues by Ricinus communis agglutinin
  作者：Alfonso Rivera-Sagredo、Jesús Jiménez-Barbero、Manuel Martín-Lomas、Dolores Solís、Teresa Díaz-Mauriño

  DOI：10.1016/0008-6215(92)80055-6

  日期：1992.8

  The 2-, 3-, 6-, 2'-, 3'-, 4'-, and 6'-deoxy derivatives and the 3-O-methyl derivative of methyl beta-lactoside have been synthesised and their binding to the galactose-specific agglutinin from Ricinus communis (RCA-120) has been investigated. The results indicate that HO-3,4,6 of the beta-D-galactopyranose moiety are the key polar groups. The main difference from the closely related ricin lectin RCA-60

  已经合成了甲基β-乳糖苷的2-，3-，6-，2'-，3'-，4'-和6'-脱氧衍生物和3-O-甲基衍生物，并且它们与半乳糖结合研究了来自蓖麻的特异性凝集素（RCA-120）。结果表明，β-D-吡喃半乳糖部分的HO-3、4、6是关键的极性基团。与紧密相关的蓖麻毒素凝集素RCA-60的主要区别在于D-吡喃葡萄糖部分的HO-6，这似乎有助于碳水化合物与RCA-60的结合而不与RCA-120的结合。
• 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：——