(-)-(2R,3R)-2,3-O-isopropylidene-2-C-methyl-D-erythrono-1,4-lactone | 18465-72-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(2R,3R)-2,3-O-isopropylidene-2-C-methyl-D-erythrono-1,4-lactone
• 英文别名: 2,3-O-isopropylidene-2-C-methyl-D-erythrono-1,4-lactone；(3aR,6aR)-Dihydro-2,2,3a-trimethylfuro[3,4-d]-1,3-dioxol-4(3aH)-one；(3aR,6aR)-2,2,3a-trimethyl-6,6a-dihydrofuro[3,4-d][1,3]dioxol-4-one
• CAS: 18465-72-0
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: IUOBLUOQEZUCIP-SVGQVSJJSA-N

物化性质

• 熔点：
  51-53 °C
• 沸点：
  253.5±35.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3R)-2,3-O-isopropylidene-2-C-methyl-D-erythrono-1,4-lactone 在 水 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 溶剂黄146 、 丙酮 为溶剂， 反应 3.0h， 生成 2-C-甲基-赤藓糖醇
  参考文献：
  名称：

  An Efficient Preparation of 2-C-Methyl-d-Erythritol 4-Phosphoric Acid and Its Derivatives

  摘要：

  DOI：

  10.1021/jo9905118
• 作为产物：
  描述：

  (-)-(3R,4R)-acetic acid 4-hydroxy-4-methyl-5-oxotetrahydrofuran-3-yl ester 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 (-)-(2R,3R)-2,3-O-isopropylidene-2-C-methyl-D-erythrono-1,4-lactone
  参考文献：
  名称：

  An efficient Amano PS-catalyzed chemo-, regio- and enantioselective hydrolysis of (±)-2,3-di-O-acetyl-2-C-methyl-d-erythrono-1,4-lactone: a facile preparation of bioactive natural products (−)-saccharinic acid lactone and potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate

  摘要：

  Saccharinic acid lactone (-)-1a is a suitable building block for the synthesis of many bioactive natural products. Amano PS-induced chemo-, regio- and enantioselective hydrolysis of diacetyl lactone (+/-)-3 has been carried out to obtain (-)-1a in 46% yield with 99% ee and diacetyl lactone (+)-3 in 49% yield with 99% ee. The Amano PS-catalyzed enantioselective acylation of (+/-)-1a with vinyl acetate as an acyl donor was relatively less efficient and furnished (-)-7 in 31% yield with 99% ee and (+)-1a in 63% yield. The conversion of (-)-1a to leaf-closing substance 2a and an attempted approach to naturally occurring compounds 1b and 2b have been also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.025

文献信息

• Carbon-branched carbohydrate chirons: synthesis of C-3 and C-4-branched sugar lactones derived from d-erythronolactone
  作者：Sarah F. Jenkinson、K. Victoria Booth、Amalia M. Estévez Reino、Graeme Horne、Ramón J. Estévez、George W.J. Fleet

  DOI：10.1016/j.tetasy.2009.08.029

  日期：2009.10

  Two carbon chain extensions using a Wittig reaction on both a 1-deoxy ribulose derivative and a C-2-branched erythrose derivative are reported. Subsequent dihydroxylation resulted in the synthesis of C-3 and C-4 methyl-branched sugar lactones, the useful synthetic building blocks. Control of the stereoselectivity of both the Wittig reaction and the dihydroxylation is investigated, and 3-C-methyl and

  报道了使用Wittig反应在1-脱氧核糖衍生物和C-2-支化赤藓糖衍生物上的两个碳链延伸。随后的二羟基化作用导致合成了C-3和C-4甲基支链糖内酯，它们是有用的合成构件。研究了Wittig反应和二羟基化反应的立体选择性的控制，并研究了3- C-甲基和4- C-甲基d-altrono-1,4-内酯和d-glucono-1,4-内酯和4- C合成了-羟甲基-d-altrono-1,4-内酯。
• Isoprenoid biosynthesis
  申请人：Eisenreich Wolfgang

  公开号：US20070015216A1

  公开（公告）日：2007-01-18

  The present invention relates to enzymatic activity involved in isoprenoid biosynthesis as well as to inhibitors, notably herbicides, for enzymes in the biosynthesis of isoprenoids. More specifically, the present invention relates to screening methods for detecting such inhibitors, and to enzymatically active proteins for performing said methods as well as purified isolated DNA coding for such proteins. Moreover, the present invention relates to novel inhibitors detectable by said screening methods as well as compositions and processes for inhibiting the synthesis of isoprenoids and for controlling the growth of organisms based on said inhibitors. The invention relates also to the development of inhibitor-resistant plant enzymes and plants, plant tissues, plant seeds and plant cells.

  本发明涉及参与异戊二烯生物合成的酶活性，以及用于异戊二烯类物质生物合成酶的抑制剂，特别是除草剂。更具体地，本发明涉及用于检测此类抑制剂的筛选方法，以及用于执行该方法的具有酶活性的蛋白质和编码该类蛋白质的纯化分离DNA。此外，本发明还涉及通过上述筛选方法检测到的新型抑制剂，以及用于抑制异戊二烯类物质合成和基于该类抑制剂控制生物生长的组合物和过程。本发明还涉及抑制剂耐药植物酶和植物、植物组织、植物种子和植物细胞的开发。
• Concise synthesis of enantiopure erythro-saccharinic acid lactone and potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate
  作者：Alexandros E. Koumbis、Apostolos D. Kaitaidis、Stefanos S. Kotoulas

  DOI：10.1016/j.tetlet.2006.09.156

  日期：2006.11

  A short and efficient approach was applied to the total synthesis of erythro-saccharinic acid lactone and the leaf-closing substance potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate from a 2-C-hydroxymethyl-D-erythrose derivative, using a combined strategy. (c) 2006 Elsevier Ltd. All rights reserved.
• ISOPRENOID BIOSYNTHESIS
  申请人：Bacher, Adelbert

  公开号：EP1198575B1

  公开（公告）日：2007-09-19
• WO2007/25304
  申请人：——

  公开号：——

  公开（公告）日：——