[5,5-2H2]-1-deoxy-D-xylose | 195379-70-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [5,5-2H2]-1-deoxy-D-xylose
• 英文别名: [5,5-2H2]-1-deoxy-D-xylulose；(3S,4R)-5,5-dideuterio-3,4,5-trihydroxypentan-2-one
• CAS: 195379-70-5
• 化学式: C₅H₁₀O₄
• 分子量: 136.116
• InChiKey: IGUZJYCAXLYZEE-RMMLTXHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 [5,5-2H2]-1-deoxy-D-xylose 在 吡啶 作用下， 生成 [5,5-2H2]-1-deoxy-D-xylulose triacetate
  参考文献：
  名称：

  实用的合成1-脱氧-d-木酮糖和1-脱氧-d-木酮糖5-磷酸酯的氘标记

  摘要：

  优化的克级合成可以生产1-deoxy-d-木酮糖和1-deoxy-d-木酮糖5-磷酸，并可能在C-5处进行氘标记。此类底物是研究甲羟戊酸非依赖性2- C-甲基-d-赤藓糖醇4-磷酸途径用于光养性真核生物细菌和叶绿体中类异戊二烯生物合成以及维生素B 1（硫胺素二磷酸）和B 6（生物素）的生物合成所必需的。磷酸吡ido醇）。

  DOI：

  10.1016/j.tet.2004.10.016
• 作为产物：
  描述：

  3,4-O-isopropylidene-1-deoxy-(5,5'-2(H)2)-D-xylulose 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以71%的产率得到[5,5-2H2]-1-deoxy-D-xylose
  参考文献：
  名称：

  Highly Efficient and Versatile Synthesis of Isotopically Labelled 1-Deoxy-D-xylulose

  摘要：

  An efficient and versatile synthesis of 1-deoxy-[4,4-H-2(2)]-D-xylulose 1b (= 1-deoxy-[4,4-H-2(2)]-D-threopentulose) from dimethyl 2,3-O-isopropylidene-D-tartrate in 31% overall yield is described. The synthetic protocol allows a flexible adaptation to other labelling patterns and isotopes. Labelled 1-deoxy-xylulose is of high value as a metabolic probe in biosynthetic studies towards terpenoids and prenylated compounds following the Rohmer pathway. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01448-2

文献信息

• 5-Hydroxypentane-2,3-dione (laurencione), a bacterial metabolite of 1-deoxy-D- threo -pentulose
  作者：Surya Rosa Putra、Lionel Charon、Knut Danielsen、Catherine Pale-Grosdemange、Luisa-Maria Lois、Narciso Campos、Albert Boronat、Michel Rohmer

  DOI：10.1016/s0040-4039(98)01301-x

  日期：1998.8
• Improved protocol towards isotopically labelled 1-deoxy-D-xylulose
  作者：Andreas Jux、Wilhelm Boland

  DOI：10.1016/s0040-4039(99)01417-3

  日期：1999.9

  An improved synthetic protocol towards 1-deoxy-[4,4-H-2(2)]-D-xylulose (1a) (= 1-deoxy-[4,4-H-2(2)]-D-threopentulose) from dimethyl 2,3-O-isopropylidene-o-tartrate (2) (44% overall yield) is described. The key-operation is a novel one-pot reductive alkylation of the protected halfester 3, by sequential treatment with superdeuteride(hydride) and methyl lithium, providing the protected 1-deoxy-D-xylulose (5) in high yield. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Practical synthesis of 1-deoxy-d-xylulose and 1-deoxy-d-xylulose 5-phosphate allowing deuterium labelling
  作者：Odile Meyer、Jean-François Hoeffler、Catherine Grosdemange-Billiard、Michel Rohmer

  DOI：10.1016/j.tet.2004.10.016

  日期：2004.12

  are required for investigations on the mevalonate-independent 2-C-methyl-d-erythritol 4-phosphate pathway for isoprenoid biosynthesis in bacteria and chloroplasts of phototrophic eukaryotes and for the biosynthesis of vitamins B1 (thiamine diphosphate) and B6 (pyridoxol phosphate) in bacteria.

  优化的克级合成可以生产1-deoxy-d-木酮糖和1-deoxy-d-木酮糖5-磷酸，并可能在C-5处进行氘标记。此类底物是研究甲羟戊酸非依赖性2- C-甲基-d-赤藓糖醇4-磷酸途径用于光养性真核生物细菌和叶绿体中类异戊二烯生物合成以及维生素B 1（硫胺素二磷酸）和B 6（生物素）的生物合成所必需的。磷酸吡ido醇）。
• Highly Efficient and Versatile Synthesis of Isotopically Labelled 1-Deoxy-D-xylulose
  作者：Jörn Piel、Wilhelm Boland

  DOI：10.1016/s0040-4039(97)01448-2

  日期：1997.9

  An efficient and versatile synthesis of 1-deoxy-[4,4-H-2(2)]-D-xylulose 1b (= 1-deoxy-[4,4-H-2(2)]-D-threopentulose) from dimethyl 2,3-O-isopropylidene-D-tartrate in 31% overall yield is described. The synthetic protocol allows a flexible adaptation to other labelling patterns and isotopes. Labelled 1-deoxy-xylulose is of high value as a metabolic probe in biosynthetic studies towards terpenoids and prenylated compounds following the Rohmer pathway. (C) 1997 Published by Elsevier Science Ltd.