6-O-Octanoyl-α-D-glucopyranose | 73174-07-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 6-O-Octanoyl-α-D-glucopyranose
• 英文别名: 6-O-Caprinoyl-D-glucopyranose；6-O-Decanoyl-alpha-D-glucopyranose；[(2R,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl decanoate
• CAS: 73174-07-9
• 化学式: C₁₆H₃₀O₇
• 分子量: 334.41
• InChiKey: WVGXAJWVJXKEID-JZYAIQKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  a-无水葡萄糖酯 、 acetone oxime decanoate 以 various solvent(s) 为溶剂， 以91%的产率得到6-O-Octanoyl-α-D-glucopyranose
  参考文献：
  名称：

  Gotor, Vicente; Pulido, Rosalino, Journal of the Chemical Society. Perkin transactions I, 1991, # 2, p. 491 - 492

  摘要：

  DOI：

文献信息

• Sugar chemistry without protecting groups-III. A facile chemical synthesis of 6-O-acyl-D-glycopyranoses and methyl-6-O-acyl-d-glycopyranosides.
  作者：Krystyna Baczko、Daniel Plusquellec

  DOI：10.1016/s0040-4020(01)80906-6

  日期：——

  Regioselective acylation of non protected glycopyranosides was performed using 3- acylthiazolidine-2-thiones 1 and the novel 3-acyl-5-methyl-1,3,4-thiadiazole-2(3H)-thiones 2 as the acylating reagents, yielding 6-O-acylated derivatives in high yields. Acylation of free α-D-glucose and α-D-galactose using the same conditions lead to the 6-O-acylglycoses. This reaction is compared with our previous synthesis

  使用3-酰基噻唑烷-2-硫酮1和新型3-酰基-5-甲基-1,3,4-噻二唑-2（3H）-硫酮2作为酰化剂，对未保护的吡喃葡萄糖苷进行区域选择性酰化，得到6 -O-酰化衍生物的产率高。在相同条件下将游离α-D-葡萄糖和α-D-半乳糖酰化，得到6-O-酰基糖。将该反应与我们先前由PD-葡萄糖合成的1-O-酰基-β-D-葡萄糖进行了比较。
• Sugar chemistry without protecting groups: a novel regioselective synthesis of 6-O-acyl-D-glucopyranoses and methyl-6-O-acyl-α--glucopyranosides
  作者：Daniel Plusquellec、Krystyna Baczko

  DOI：10.1016/s0040-4039(00)96390-1

  日期：1987.1

  hydroxyl groups of α--glucose and methyl-α--glucoside were selectively esterified by treating the free sugars with -acylthiazolidine-2-thiones, thus affording respectively 6--acyl--glucopyranoses and methyl-6--acyl-α--glucopyranosides in high yields. This new reaction is compared with our previous synthesis of 1--acyl-β--glucopyranoses from β--glucose and interpreted in terms of anomeric effect.

  通过用-酰基噻唑烷-2-硫酮处理游离糖，选择性地酯化α-葡萄糖和甲基-α-葡萄糖苷的伯羟基，分别得到6-酰基-葡萄糖吡喃糖和甲基-6-酰基- α--吡喃葡萄糖苷的产率高。将该新反应与我们先前从β-葡萄糖合成1-酰基-β-葡萄糖吡喃糖进行了比较，并根据异头作用进行了解释。
• Yoshimoto,K. et al., Chemical and pharmaceutical bulletin, 1979, vol. 27, # 11, p. 2661 - 2674
  作者：Yoshimoto,K. et al.

  DOI：——

  日期：——
• GOTOR, VICENTE;PULIDO, ROSALINO, J. CHEM. SOC. PERKIN TRANS. PT 1,(1991) N, C. 491-492
  作者：GOTOR, VICENTE、PULIDO, ROSALINO

  DOI：——

  日期：——
• PLUSQUELLEC, DANIEL;BACZKO, KRYSTYNA, TETRAHEDRON LETT., 28,(1987) N 33, 3809-3812
  作者：PLUSQUELLEC, DANIEL、BACZKO, KRYSTYNA

  DOI：——

  日期：——