2,3,6,2',3',4',6'-hepta-O-acetyl-isocyanato-β-D-lactose | 888702-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,6,2',3',4',6'-hepta-O-acetyl-isocyanato-β-D-lactose
• 英文别名: hepta-O-acetyl-β-lactosyl isocyanate；hepta-O-acetyl-β-D-lactosyl isocyanate；1-hepta-O-acetyl-β-D-lactosyl isocyanate；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-isocyanato-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 888702-68-9
• 化学式: C₂₇H₃₅NO₁₈
• 分子量: 661.571
• InChiKey: KTBWUGAGUCYCJX-FDXOKOSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  241
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2,3,6,2',3',4',6'-hepta-O-acetyl-isocyanato-β-D-lactose 、 甲醇 反应 3.0h， 以63.76%的产率得到(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-((methoxycarbonyl)amino)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Dandale; Deshmukh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 4, p. 613 - 618

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(间甲苯基)甲磺酰胺 、 lead cyanate 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 3.0h， 生成 2,3,6,2',3',4',6'-hepta-O-acetyl-isocyanato-β-D-lactose
  参考文献：
  名称：

  Ghayalkar, Renu B.; Deshmukh, Shirish P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 4, p. 525 - 530

  摘要：

  DOI：

文献信息

• New synthetic approach to per-O-acetyl-isocyanates, isothiocyanates and thioureas in the disaccharide and cyclodextrin series
  作者：Stephane Menuel、Stanislaw Porwanski、Alain Marsura

  DOI：10.1039/b600023a

  日期：——

  An efficient method for the preparation of per-O-acetyl disaccharides and cyclodextrin isocyanates or isothiocyanates by the phosphine imide strategy is reported. Successful one-pot, high yield syntheses of cellobiose, lactose and sucrose isocyanates or/and isothiocyanates pure β-anomers have been completed starting from their corresponding monoazido-per-O-acetyl derivatives. Transformation of the ACEtris-6-azido-per-O-methylated and the ACEtris-6-azido-per-O-acetylated-α-cyclodextrins or of the 6A-azido-6A-deoxy-per-O-acetyl-β-cyclodextrin into the corresponding isocyanates and/or isothiocyanates is also presented. Finally the conversion of the cyclodextrin isothiocyanates by nucleophilic addition of primary and secondary amines into a large panel of original thioureido-cyclodextrins derivatives is described.

  报告了一种通过膦酰亚胺策略制备过 O-乙酰基二糖和环糊精异氰酸酯或异硫氰酸盐的高效方法。从相应的单叠氮过-O-乙酰基衍生物开始，成功地完成了纤维生物糖、乳糖和蔗糖异氰酸酯或/和异硫氰酸盐纯 β-异构体的单锅高产合成。此外，还介绍了 ACEtris-6-azido-per-O-methylated 和 ACEtris-6-azido-per-O-acetylated-α-cyclodextrin 或 6A-azido-6A-deoxy-per-O-acetyl-β-cyclodextrin 转化为相应的异氰酸酯和/或异硫氰酸盐的情况。最后还介绍了通过伯胺和仲胺的亲核加成将环糊精异硫氰酸酯转化为大量硫代环糊精原始衍生物的过程。
• Dandale; Deshmukh, Journal of the Indian Chemical Society, 2007, vol. 84, # 12, p. 1266 - 1268
  作者：Dandale、Deshmukh

  DOI：——

  日期：——
• Synthesis of N- and S-bis-protected lactosyl isothiobiurets
  作者：Anvita S. Dandale、Dattatraya V. Mangte、Shirish P. Deshmukh

  DOI：10.1016/j.carres.2006.11.025

  日期：2007.4

  Several NS-bis(hepta-O-acetyllactosyl)-1-aryl-2-isothiobiuret compounds have been synthesised for the first time by the reaction of S-(hepta-O-acetyl-beta-lactosyl)-1-arylisothiocarbamides and hepta-O-acetyl-beta-lactosyl isocyanate. The identities of these newly synthesised compounds were established on the basis of elemental analysis and IR, H-1 NMR, C-13 NMR and mass spectral studies. (c) 2006 Elsevier Ltd. All rights reserved.