2-methoxy-5-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 42344-69-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methoxy-5-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: 2-Methoxy-4-formylphenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosid；4-methoxy-3-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzaldehyde；5-formyl-2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(5-formyl-2-methoxyphenoxy)oxan-2-yl]methyl acetate
• CAS: 42344-69-4
• 化学式: C₂₂H₂₆O₁₂
• 分子量: 482.441
• InChiKey: NUZRCGHCJJERSY-QMCAAQAGSA-N

物化性质

• 熔点：
  144-146 °C(Solv: ethanol (64-17-5))
• 沸点：
  568.2±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-methoxy-5-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 二正丁基氧化锡 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 27.0h， 生成 [4-methoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate
  参考文献：
  名称：

  Studies on the Synthesis and Antiproliferative Activities of 13‐cis‐Retinoyl Sugar Derivatives

  摘要：

  New retinoyl sugar derivatives of 13-cis-retinoic acid were synthesized in three ways in this paper in order to enhance pharmacal effects, especially antiproliferative activities of 13-cis-retinoic acid. Their structures were confirmed by IR, H-1-NMR, C-13-NMR, and MS spectra and their antiproliferative activities were determined in vitro using human cancer lines. Results showed that some compounds possessed potential antitumor activities.

  DOI：

  10.1080/07328300600966497
• 作为产物：
  描述：

  异香兰素 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 吡啶 、 silver(l) oxide 作用下， 生成 2-methoxy-5-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Casparis et al., Pharmaceutica Acta Helvetiae, 1946, vol. 21, p. 341,344

  摘要：

  DOI：

文献信息

• ——
  作者：A. E. Pavlov、V. M. Sokolov、V. I. Zakharov

  DOI：10.1023/a:1013971214679

  日期：——

  A series of acetylated aryl beta-D-glucopyranos ides were prepared in 12-63% yields from tetra-O-acetyl-alpha-D-glycopyranosyl bromide and phenols containing acyl, formyl, and hydroxy substituents, and also from sterically hindered phenols in the two-phase system chloroform-aqueous alkali in the presence of triethylbenzylammonium chloride. Hydroxyethylated sucrose and dibenzo-18-crown-6 do not behave as phase-transfer catalysts in glycosylation of phenols.
• Jain, S. M.; Devi, Sunita; Bani, S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1019 - 1023
  作者：Jain, S. M.、Devi, Sunita、Bani, S.、Singh, Surjit、Singh, G. B.

  DOI：——

  日期：——
• Jain, S M; Khajuria, R K; Dhar, K L, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 11, p. 1037 - 1040
  作者：Jain, S M、Khajuria, R K、Dhar, K L、Singh, Surjeet、Bani, S、et al.

  DOI：——

  日期：——
• Jain, S. M.; Khajuria, R. K.; Dhar, K. L., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 8, p. 805 - 807
  作者：Jain, S. M.、Khajuria, R. K.、Dhar, K. L.、Singh, Surjeet、Singh, G. B.

  DOI：——

  日期：——
• Jain; Kant; Devi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 1, p. 95 - 97
  作者：Jain、Kant、Devi、Dahr、Singh、Bani、Sing h

  DOI：——

  日期：——