2,3-O-isopropylidene-L-erythrouronic acid | 1056473-59-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-L-erythrouronic acid
• 英文别名: 2,3-O-isopropylidene-L-erythuronolactone；2,3-O-isopropylidene-L-erythruronolactone；(3a,6aS)-6-hydroxy-2,2-dimethylperhydrofuro[3,4-d][1,3]dioxol-4-one；(3aR,6aS)-Dihydro-6-hydroxy-2,2-dimethyl-furo[3,4-d]-1,3-dioxol-4(3aH)-one；(3aR,6aS)-6-hydroxy-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 1056473-59-6
• 化学式: C₇H₁₀O₅
• 分子量: 174.153
• InChiKey: UPFMNKGFLNXERP-PYHARJCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-L-erythrouronic acid 在 正丁基锂 、 二苯甲酮 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 (-)-(2R,3R,4R)-2,3-dihydroxy-2,3-O-isopropylidene-4-hydroxymethylcyclopentan-1-one
  参考文献：
  名称：

  Carbocyclic analogues of d-ribose-5-phosphate: Synthesis and behavior with 5-phosphoribosyl α-1-pyrophosphate synthetases

  摘要：

  The synthesis of cyclopentyl and cyclopentenyl analogues of the cr-anomer of D-ribose-5-phosphate from D-ribonolactone and D-ribose is described. These analogues, which have the same absolute configuration as D-ribose-5-phosphate, were incubated with PRPP synthetases in an attempt to prepare the corresponding carbocyclic PRPP analogues. The carbocyclic ribose-5-phosphate analogues were found to be inhibitors, rather than substrates, for 5-phosphoribosyl alpha-1-pyrophosphate synthetases of both bacterial and human origin. The inhibitory behavior of the analogues is described. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00090-9
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 sodium hydroxide 、 sodium periodate 作用下， 以 水 为溶剂， 反应 0.25h， 以72%的产率得到2,3-O-isopropylidene-L-erythrouronic acid
  参考文献：
  名称：

  由2,3-O-异亚丙基-L-赤藓糖酸内酯通过Tebbe介导的级联反应合成4a-氨基甲酸酯-α-D-呋喃糖。

  摘要：

  通过Tebbe试剂的一锅法转换，涉及一种由D-核糖合成1,2,3,5-四乙酰基氨基甲酸-α-D-呋喃糖的新的，高效的和非对映选择性的方法，涉及级联反应顺序为甲基化，异丙基裂解，碳环化和再次甲基化。

  DOI：

  10.1039/b802418a

文献信息

• A total synthesis of (+)-isovelleral. The absolute configuration of the russulaceae sesquiterpenes
  作者：R. Bergman、T. Hansson、O. Sterner、B. Wickberg

  DOI：10.1039/c39900000865

  日期：——

  (+)-Isovelleral, an antibiotic and antifeedant sesquiterpene dialdehyde from Basidiomycetes, has been synthesised via a diastereoselective intramolecular Diels–Alder cyclisation of a chiral intermediate derived from D-ribonolactone.

  （+）-Isovelleral是来自担子菌的抗生素和拒食性倍半萜烯二醛，它是通过非对映选择性分子内Diels-Alder环化衍生自D-核糖内酯的手性中间体而合成的。
• A convenient procedure for the synthesis of chiral 6,7-dihydroxy-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones
  作者：Yakdhane Kacem、Béchir Ben Hassine

  DOI：10.1016/j.tetasy.2013.12.002

  日期：2014.2

  The cyclocondensation reactions between L-alpha-amino acid phenylhydrazides and 2,3-O-isopropylidene-L-erythruronolactone in the presence of a catalytic amount of p-toluenesulfonic acid afforded diastereomerically pure (3S,6R,7R,7aS)-3-substituted-6,7-isopropylidenedioxy-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones, which were converted by acidic hydrolysis with MeOH-HCl into their corresponding optically active (35,6R,7R,7aS)-3-substituted-6,7-dihydroxy-l-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones in good yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Carbocyclic analogues of d-ribose-5-phosphate: Synthesis and behavior with 5-phosphoribosyl α-1-pyrophosphate synthetases
  作者：Ronald J. Parry、Mark R. Burns、Phillip N. Skae、Jeffrey C. Hoyt、Biman Pal

  DOI：10.1016/0968-0896(96)00090-9

  日期：1996.7

  The synthesis of cyclopentyl and cyclopentenyl analogues of the cr-anomer of D-ribose-5-phosphate from D-ribonolactone and D-ribose is described. These analogues, which have the same absolute configuration as D-ribose-5-phosphate, were incubated with PRPP synthetases in an attempt to prepare the corresponding carbocyclic PRPP analogues. The carbocyclic ribose-5-phosphate analogues were found to be inhibitors, rather than substrates, for 5-phosphoribosyl alpha-1-pyrophosphate synthetases of both bacterial and human origin. The inhibitory behavior of the analogues is described. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of 4a-carba-α-d-lyxofuranose from 2,3-O-isopropylidene-l-erythruronolactone via Tebbe-mediated cascade reaction
  作者：Girija Prasad Mishra、G. Venkata Ramana、B. Venkateswara Rao

  DOI：10.1039/b802418a

  日期：——

  approach for the synthesis of 1,2,3,5-tetraacetylcarba-alpha-D-lyxofuranose from D-ribose is reported via one-pot conversion of to using Tebbe reagent which involves a cascade reaction sequence of methylenation, cleavage of isopropyl group, carbocyclization and again methylenation.

  通过Tebbe试剂的一锅法转换，涉及一种由D-核糖合成1,2,3,5-四乙酰基氨基甲酸-α-D-呋喃糖的新的，高效的和非对映选择性的方法，涉及级联反应顺序为甲基化，异丙基裂解，碳环化和再次甲基化。