4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl chloride | 77838-20-1

• 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: 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl chloride
• 英文别名: 2-deoxy-3,7-anhydro-4,5,6,8-tetra-O-acetyl-D-glucooctonyl chloride；[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-(2-chloro-2-oxoethyl)oxan-2-yl]methyl acetate
• CAS: 77838-20-1
• 化学式: C₁₆H₂₁ClO₁₀
• 分子量: 408.79
• InChiKey: IMXJLGMBLQKTNW-FHXAZYNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl chloride 在 盐酸羟胺 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 diethyl ester of 1-oximino-2-desoxy-3,7-anhydro-4,5,6,8-tetra-O-acetyl-D-glucooctylphosphonic acid
  参考文献：
  名称：

  Zhdanov, Yu. A.; Uzlova, L. A.; Glebova, Z. I., Doklady Chemistry, 1980, vol. 255, p. 552 - 555

  摘要：

  DOI：
• 作为产物：
  描述：

  2-desoxy-3,7-anhydro-4,5,6,8-tetra-O-acetyl-D-glucooctonic acid 在 氯化亚砜 作用下， 反应 2.0h， 生成 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl chloride
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiomerically enriched aminoalkenols and glycosides thereof

  摘要：

  1-t-Butoxycarbonylamido-3-pentene-1-ol 3 and 2-azido-4-phenyl-3-butene-1-ol 4 were enantiomerically enriched by enzymatic acetylation using various lipases and esterases (CHIRAZYM) to give acetylated compounds 5 and 7, respectively. Compound 3 gave the best results (E = 94) with Candida antarctica A lipase (CHIRAZYM L-5), whereas 4 could not be separated into the enantiomers with satisfactory E values. The absolute configurations were proven for both compounds via independently prepared derivatives. Both enantiomers of 5, as well as racemic 7, were N-deblocked and condensed with octonic acid derivatives 14 to give the corresponding C-glycosides 17 and 22 after deprotection of the intermediates in good overall yield. Compound 4 was similarly condensed with glucose imidate 11 to give the diastereomeric O-glycosides 13 after deprotection. The latter glycosides were prepared as precursors for the generation of the corresponding aldehydes as substrates for aldolase catalyzed reactions. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00294-9

文献信息

• Tolstikov, G. A.; Spivak, A. Yu.; Kresteleva, I. V., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 1.2, p. 134 - 140
  作者：Tolstikov, G. A.、Spivak, A. Yu.、Kresteleva, I. V.、Spirikhin, L. V.、Sultanova, V. S.

  DOI：——

  日期：——
• TOLSTIKOV, G. A.;SPIVAK, A. YU.;KRESTELEVA, I. V.;SPIRIXIN, L. V.;SULTANO+, ZH. ORGAN. XIMII, 25,(1989) N, S. 149-155
  作者：TOLSTIKOV, G. A.、SPIVAK, A. YU.、KRESTELEVA, I. V.、SPIRIXIN, L. V.、SULTANO+

  DOI：——

  日期：——