1-Deoxy-3,4,5,6,7-penta-O-acetyl-L-gulo-2-heptulose | 83615-60-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-Deoxy-3,4,5,6,7-penta-O-acetyl-L-gulo-2-heptulose
• 英文别名: heptulose；penta-O-acetyl-keto-D-gluco-1-deoxy-[2]heptulose；Penta-O-acetyl-keto-D-gluco-1-desoxy-[2]heptulose；[(2R,3R,4S,5R)-2,3,4,5-tetraacetyloxy-6-oxoheptyl] acetate
• CAS: 83615-60-5
• 化学式: C₁₇H₂₄O₁₁
• 分子量: 404.371
• InChiKey: UQHQSDJOURUWPM-YYIAUSFCSA-N

物化性质

• 熔点：
  91-92 °C(Solv: water (7732-18-5); ethanol (64-17-5); acetone (67-64-1))
• 沸点：
  484.9±45.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.13
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  148.57
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  2,3,4,5,6-penta-O-acetyl-D-gluconoyl chloride 在 二氯乙基铝 、 镍 作用下， 以 乙醇 为溶剂， 反应 6.5h， 生成 1-Deoxy-3,4,5,6,7-penta-O-acetyl-L-gulo-2-heptulose
  参考文献：
  名称：

  Tolstikov, G. A.; Spivak, A. Yu.; Kresteleva, I. V., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 11.1, p. 2111 - 2116

  摘要：

  DOI：

文献信息

• The Action of Diazomethane on the Pentaacetates of aldehydo-D-Glucose and aldehydo-D-Galactose¹
  作者：M. L. Wolfrom、D. I. Weisblat、Evan F. Evans、J. B. Miller

  DOI：10.1021/ja01581a025

  日期：1957.12
• Tin- and indium-mediated allylation in aqueous media: application to unprotected carbohydrates
  作者：Enoch Kim、Dana M. Gordon、Walther Schmid、George M. Whitesides

  DOI：10.1021/jo00072a038

  日期：1993.9

  The convenient and efficient indium- and tin-mediated allylation method for extending the carbon chain of unprotected carbohydrates is illustrated by preparation of 4-6 and 9-10. Various 2-deoxyaldoses can be synthesized by the allylation of aldoses. Indium-mediated reactions between ethyl 2-(bromomethyl)acrylate and aldoses provide access to 2-keto-3-deoxyulosonic acids. These reactions are diastereoselective; the major product contains a threo relationship between the newly generated hydroxyl group and the C-2 hydroxyl group of the starting carbohydrate. Results obtained from reactions involving authentic organotin and organoindium reagents and from the corresponding heterogeneous reactions are similar.
• TOLSTIKOV, G. A.;SPIVAK, A. YU.;KRESTELEVA, I. V.;VYRYPAEV, E. M., ZH. ORGAN. XIMII, 25,(1989) N1, S. 2342-2348
  作者：TOLSTIKOV, G. A.、SPIVAK, A. YU.、KRESTELEVA, I. V.、VYRYPAEV, E. M.

  DOI：——

  日期：——