acetic acid 4,5-diacetoxy-2-acetoxymethyl-1-acetylpiperidin-3-yl | 19130-97-3

• 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: acetic acid 4,5-diacetoxy-2-acetoxymethyl-1-acetylpiperidin-3-yl
• 英文别名: peracetyl-1-deoxynojirimycin；1,5-Imino-N-acetyl-2,3,4,6-tetra-O-acetyl-1,5-didesoxy-D-glucit；2,3,4,6-Tetra-O-acetyl-N-acetyl-1-desoxynojirimycin, 1,5-Imino-N-acetyl-2,3,4,6-tetra-O-acetyl-1,5-didesoxy-D-glucit；[(2R,3R,4R,5S)-1-acetyl-3,4,5-triacetyloxypiperidin-2-yl]methyl acetate
• CAS: 19130-97-3
• 化学式: C₁₆H₂₃NO₉
• 分子量: 373.36
• InChiKey: UWAXKEPCPIIJKB-QKPAOTATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  acetic acid 4,5-diacetoxy-2-acetoxymethyl-1-acetylpiperidin-3-yl 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以70%的产率得到N-acetyl-1-deoxynojirimycin
  参考文献：
  名称：

  Glucose is a Precursor of 1-deoxynojirimycin and 1-deoxymannonojirimycin in Streptomyces subrutilus

  摘要：

  Streptomyces subrutilus ATCC 27467, when grown on a glucose-containing soyabean medium, produces both 1-deoxymannonojirimycin (DMJ) and 1-deoxynojirimycin (DNJ) in its culture medium. When 1- or 2-[H-2]-D-glucose is used, the deuterium label appears at C6 in both alkaloids and the labelling pattern suggests that the first step in the biosynthesis of both DNJ and DMJ is a glucose to fructose isomerisation. Studies with 5-[H-2]- and 6,6-[H-2(2)]-D-glucose indicate that oxidation of the 6-position of the glucose/fructose occurs during the biosynthesis and that mannonojirimycin is the first aminosugar to be formed. Mannonojirimycin can then undergo dehydration and reduction to DMJ. Alternatively, epimerisation of mannonojirimycin can occur at C2 to give norjirimycin which is then dehydrated and reduced to DNJ.

  DOI：

  10.1016/s0040-4020(01)88220-x
• 作为产物：
  描述：

  Sphingofungin D 在 吡啶 、 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 锂硼氢 、 氢氟酸 、 sodium hydride 、 碳酸氢钠 、 臭氧 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 acetic acid 4,5-diacetoxy-2-acetoxymethyl-1-acetylpiperidin-3-yl
  参考文献：
  名称：

  确定鞘氨醇A，B，C和D的相对和绝对立体化学

  摘要：

  通过刚性双环衍生物5的光谱分析以及使用2S特异性的4的酶促水解作用，最近分离出的鞘氨醇单糖的2、3、4和5位的相对和绝对立体化学已确定为2S，3R，4R，5S。酰基转移酶。这些构型分配已通过降解和鞘氨醇单丁胺B转化为过乙酰基脱氧野oji霉素6证实。

  DOI：

  10.1016/s0040-4039(00)74115-3

文献信息

• A Short and Simple Synthesis of 1-Deoxynojirimycin Derivatives from<scp>d</scp>-Glucose
  作者：Sukhendu B. Mandal、Ashim Roy、Basudeb Achari

  DOI：10.1055/s-2006-926369

  日期：——

  Insertion of an amino functionality at C-5 of d-glucose with inversion of configuration, followed by imine formation with the latent aldehyde at C-1 and concomitant reduction furnished the 1-deoxynojirimycin skeleton.

  在d-葡萄糖的C-5位置插入氨基功能，伴随构型反转，然后与C-1处的潜在醛形成亚胺并同时还原，最终获得了1-去氧诺吉霉素骨架。
• Glucose is a Precursor of 1-deoxynojirimycin and 1-deoxymannonojirimycin in Streptomyces subrutilus
  作者：David J Hardick、David W. Hutchinson、Sally J. Trew、Elizabeth M.H. Wellington

  DOI：10.1016/s0040-4020(01)88220-x

  日期：1992.1

  Streptomyces subrutilus ATCC 27467, when grown on a glucose-containing soyabean medium, produces both 1-deoxymannonojirimycin (DMJ) and 1-deoxynojirimycin (DNJ) in its culture medium. When 1- or 2-[H-2]-D-glucose is used, the deuterium label appears at C6 in both alkaloids and the labelling pattern suggests that the first step in the biosynthesis of both DNJ and DMJ is a glucose to fructose isomerisation. Studies with 5-[H-2]- and 6,6-[H-2(2)]-D-glucose indicate that oxidation of the 6-position of the glucose/fructose occurs during the biosynthesis and that mannonojirimycin is the first aminosugar to be formed. Mannonojirimycin can then undergo dehydration and reduction to DMJ. Alternatively, epimerisation of mannonojirimycin can occur at C2 to give norjirimycin which is then dehydrated and reduced to DNJ.
• Determination of the relative and absolute stereochemistry of sphingofungins A, B, C, and D
  作者：VanMiddlesworth Frank、Claude Dufresne、Francine E. Wincott、Ralph T. Mosley、Kenneth E. Wilson

  DOI：10.1016/s0040-4039(00)74115-3

  日期：1992.1

  The relative and absolute stereochemistry of positions 2, 3, 4, and 5 of the recently isolated sphingofungins has been determined as 2S, 3R, 4R, 5S by spectral analysis of the rigid bicyclic derivative 5, and enzymatic hydrolysis of 4 using a 2S specific acylase. These configurational assignments were confirmed by degradation and conversion of sphingofungin B to peracetyl deoxynojirimycin 6.

  通过刚性双环衍生物5的光谱分析以及使用2S特异性的4的酶促水解作用，最近分离出的鞘氨醇单糖的2、3、4和5位的相对和绝对立体化学已确定为2S，3R，4R，5S。酰基转移酶。这些构型分配已通过降解和鞘氨醇单丁胺B转化为过乙酰基脱氧野oji霉素6证实。