dimethyl 2,6-anhydro-3-deoxy-D-ribo-hept-2-enarate | 658078-71-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: dimethyl 2,6-anhydro-3-deoxy-D-ribo-hept-2-enarate
• 英文别名: dimethyl (2S,3S,4S)-3,4-dihydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylate
• CAS: 658078-71-8
• 化学式: C₉H₁₂O₇
• 分子量: 232.19
• InChiKey: VFCWFXLZQMMDET-QTSITTDLSA-N

物化性质

• 沸点：
  352.0±42.0 °C(Predicted)
• 密度：
  1.469±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  氯化苄 、 dimethyl 2,6-anhydro-3-deoxy-D-ribo-hept-2-enarate 在 吡啶 作用下， 反应 4.0h， 以74%的产率得到dimethyl 2,6-anhydro-4,5-di-O-benzoyl-3-deoxy-D-ribo-hept-2-enarate
  参考文献：
  名称：

  (−)-Daucic acid: Proof of d-lyxo configuration, synthesis of its d-ribo, d-xylo, l-arabino and l-lyxo analogs, and biosynthetic implications

  摘要：

  The dimethyl esters of the 2,6-anhydro-3-deoxy-hept-2-enaric acids with D-xylo, D-lyxo, L-arabino, L-lyxo- and D-ribo-configuration were synthesized from D-galactose and D-mannose, respectively, and further characterized by their di-O-acetyl and di-O-benzoyl derivatives. Comparison of their physical data with those of Daucus carota derived products revealed (-)-daucic acid to have D-lyxo-configuration 46 rather than the previously assigned D-xylo stereochemistry 1. Dimethyl daucate 43 could be converted by acid-induced ring contraction and dehydration into naturally occurring (+)-osbeckic acid 47, thereby proving its (S)-configuration. Configurational identity in the pyranoid rings of (-)-daucic acid and KDO, together with available biosynthetic evidence on chelidonic acid 4, a leaf closing factor, suggests a joint, KDO 8-P-based pathway for their biosynthesis in plants. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.007
• 作为产物：
  描述：

  C-(tetra-O-acetyl-α-D-mannopyranosyl)cyanide 在 吡啶 、 盐酸 、 aluminum oxide 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 lutidine 、 硫酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 58.5h， 生成 dimethyl 2,6-anhydro-3-deoxy-D-ribo-hept-2-enarate
  参考文献：
  名称：

  （-）-Daucic acid：构型，合成和生物合成含义的修订。

  摘要：

  DOI：

  10.1002/anie.200352718

文献信息

• (−)-Daucic Acid: Revision of Configuration, Synthesis, and Biosynthetic Implications
  作者：Frieder W. Lichtenthaler、Katsumi Nakamura、Jürgen Klotz

  DOI：10.1002/anie.200352718

  日期：2003.12.8
• (−)-Daucic acid: Proof of d-lyxo configuration, synthesis of its d-ribo, d-xylo, l-arabino and l-lyxo analogs, and biosynthetic implications
  作者：Frieder W. Lichtenthaler、Jürgen Klotz、Katsumi Nakamura

  DOI：10.1016/j.tetasy.2003.10.007

  日期：2003.12

  The dimethyl esters of the 2,6-anhydro-3-deoxy-hept-2-enaric acids with D-xylo, D-lyxo, L-arabino, L-lyxo- and D-ribo-configuration were synthesized from D-galactose and D-mannose, respectively, and further characterized by their di-O-acetyl and di-O-benzoyl derivatives. Comparison of their physical data with those of Daucus carota derived products revealed (-)-daucic acid to have D-lyxo-configuration 46 rather than the previously assigned D-xylo stereochemistry 1. Dimethyl daucate 43 could be converted by acid-induced ring contraction and dehydration into naturally occurring (+)-osbeckic acid 47, thereby proving its (S)-configuration. Configurational identity in the pyranoid rings of (-)-daucic acid and KDO, together with available biosynthetic evidence on chelidonic acid 4, a leaf closing factor, suggests a joint, KDO 8-P-based pathway for their biosynthesis in plants. (C) 2003 Elsevier Ltd. All rights reserved.