3,4-O-isopropylidene-1-deoxy-(5,5'-2(H)2)-D-xylulose | 195379-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-O-isopropylidene-1-deoxy-(5,5'-2(H)2)-D-xylulose
• 英文别名: 1-[(4S,5R)-5-[dideuterio(hydroxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethanone
• CAS: 195379-72-7
• 化学式: C₈H₁₄O₄
• 分子量: 176.181
• InChiKey: RCGNXIXKZOSMQM-RKMLNCROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-O-isopropylidene-1-deoxy-(5,5'-2(H)2)-D-xylulose 在 2,6-二甲基吡啶 、 Amberlite IR 120 H⁽¹⁺⁾ 、 溴 、 三乙基碳酸氢铵缓冲液 作用下， 以 水 、 乙腈 为溶剂， 反应 51.17h， 生成 [5,5-2H2]-1-deoxy-D-xylulose-5-phosphate
  参考文献：
  名称：

  Synthesis of [5,5-2H2]-1-Deoxy-D-xylulose-5-phosphate

  摘要：

  [5,5-H-2(2)]-1-Deoxy-D-xylulose-5-phosphate was synthetically prepared. (C) 1999 Elsevier Science Ltd. All lights reserved.

  DOI：

  10.1016/s0040-4039(99)01039-4
• 作为产物：
  描述：

  methyl (4S,5S)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid-5-carboxylate 在 硼氘化锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3,4-O-isopropylidene-1-deoxy-(5,5'-2(H)2)-D-xylulose
  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

• 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.
• Synthesis of [5,5-2H2]-1-Deoxy-D-xylulose-5-phosphate
  作者：Rolf Thiel、Klaus-Peter Adam

  DOI：10.1016/s0040-4039(99)01039-4

  日期：1999.7

  [5,5-H-2(2)]-1-Deoxy-D-xylulose-5-phosphate was synthetically prepared. (C) 1999 Elsevier Science Ltd. All lights reserved.
• 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.