(3aR,6aS)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6(5H)-one | 34693-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,6aS)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6(5H)-one
• 英文别名: 1,2-O-isopropylidene-3-deoxy-3-keto-β-L-threofuranose；1,2-O-isopropylidene-α-D-glycero-tetrose-3-ulose；3-oxo-1,2-O-isopropylidene-α-D-erythrofuranose；1,2-O-isopropylidene-D-glycero-tetrafuranos-3-ulose；1,2-O-Isopropyliden-D-glycero-tetros-3-ulose；(3aR,6aS)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-one
• CAS: 34693-28-2
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: DTQCCMQTJJPRAU-PHDIDXHHSA-N

物化性质

• 沸点：
  226.6±40.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 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：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,6aS)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6(5H)-one 在 四氧化锇 、 2-甲基-2-丁醇 、 sodium hydride 、 二正丁基氧化锡 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 丙酮 、 甲苯 为溶剂， 反应 9.0h， 生成 (-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol
  参考文献：
  名称：

  具有2'-羟基的D-和L-api核苷类似物的合成作为潜在的抗HIV药物。

  摘要：

  本工作描述了从D-半乳糖开始的经由普通中间体9的具有2'-羟基的D-和L-apio-2'，3'-二脱氧核苷类似物4和5的不对称合成。通过自由基转化的立体选择性二羟基化和脱氧被成功地合成了具有D-apio结构的关键中间体12，而立体选择性的氢硼化-氧化被用于合成了另一个具有L-apio结构的关键中间体18。

  DOI：

  10.1016/j.bmc.2003.12.002
• 作为产物：
  描述：

  (3aR,6S,6aR)-6-hydroxy-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到(3aR,6aS)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6(5H)-one
  参考文献：
  名称：

  通过高立体选择性烯烃交叉复分解反应合成（E）-3'-膦烯基改性的核苷膦酸酯

  摘要：

  报道了具有（E）-3'-膦烯基和3'-膦烷基修饰的具有β- d-呋喃呋喃糖部分的核苷类似物的合成。进行高度立体选择性的烯烃交叉复分解反应，以绝对的（E）选择性在糖部分的3'-位置引入膦酰基烯基。通过脱水分子内环化反应合成了3'-膦酰基乙基-β- d-赤藓呋喃糖基核苷的3'，6'-环一膦酸。合成的化合物均未显示出针对HIV，HCV和RSV的显着体外活性。

  DOI：

  10.1021/jo200033p

文献信息

• Synthesis of (<i>E</i>)-3′-Phosphonoalkenyl Modified Nucleoside Phosphonates via a Highly Stereoselective Olefin Cross-Metathesis Reaction
  作者：Qiuya Huang、Piet Herdewijn

  DOI：10.1021/jo200033p

  日期：2011.5.20

  The synthesis of (E)-3′-phosphonoalkenyl and 3′-phosphonoalkyl modified nucleoside analogues with a β-d-erythrofuranose moiety is reported. The highly stereoselective olefin cross-metathesis reaction was applied to introduce the phosphonoalkenyl group at the 3′-position of the sugar moiety with absolute (E)-selectivity. The 3′,6′-cyclomonophosphonic acids of 3′-phosphonoethyl-β-d-erythrofuranosyl nucleosides

  报道了具有（E）-3'-膦烯基和3'-膦烷基修饰的具有β- d-呋喃呋喃糖部分的核苷类似物的合成。进行高度立体选择性的烯烃交叉复分解反应，以绝对的（E）选择性在糖部分的3'-位置引入膦酰基烯基。通过脱水分子内环化反应合成了3'-膦酰基乙基-β- d-赤藓呋喃糖基核苷的3'，6'-环一膦酸。合成的化合物均未显示出针对HIV，HCV和RSV的显着体外活性。
• Stereoselective syntheses of the methylene- and α-fluoromethylene-phosphonate analogues of 2-phospho-<scp>D</scp>-glyceric acid
  作者：G. Michael Blackburn、Abdul Rashid

  DOI：10.1039/c39880000317

  日期：——

  enantioselective synthesis is described for the preparation of (2R)-2-carboxy-3-hydroxypropane-1-phosphonic acid (1), an isosteric analogue of 2-phospho-D-glyceric acid (2), from L-threose; the route is extended to provide diastereoselective syntheses of both (1R,2R)- and (1S,2R)-2-carboxy-1-fluoro-3-hydroxypropane-1-phosphonic acids (3) and (4) respectively which provide the first examples of the synthesis of

  描述了对映选择性合成，用于从L-苏糖制备（2 R）-2-羧基-3-羟基丙烷-1-膦酸（1），2-磷酸-D-甘油酸（2）的等排类似物。; 扩展了该途径以提供（1 R，2 R）-和（1 S，2 R）-2-羧基-1-氟-3-氟丙烷-1-膦酸（3）和（4）的非对映选择性合成分别提供了在C-1处具有确定的手性的α-氟代链烷膦酸酯的合成的第一个实例。
• Conformationally Constrained Analogues of Diacylglycerol. 11. Ultrapotent Protein Kinase C Ligands Based on a Chiral 5-Disubstituted Tetrahydro-2-furanone Template
  作者：Jeewoo Lee、Shaomeng Wang、George W. A. Milne、Rajiv Sharma、Nancy E. Lewin、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm950277n

  日期：1996.1.1

  of PK-C with DAG is stereospecific, it was anticipated that PK-C would bind tightly to only one enantiomeric form of the compounds constructed with this new lactone template. Separation of enantiomers by chiral HPLC was discarded due to the ease with which acyl migration occurs in these class of compounds, and a total chiral synthesis was undertaken. Prior to chemical synthesis, the selection of the

  以前显示在外消旋5（-）[（（酰氧基）-甲基] -5-（羟甲基）四氢-2-呋喃酮）模板上构象受限的二酰基甘油（DAG）类似物具有出色的结合蛋白激酶C（PK- C）。由于PK-C与DAG的相互作用是立体特异性的，因此可以预期，PK-C仅与该新内酯模板构建的化合物的仅一种对映体形式紧密结合。由于在这类化合物中容易发生酰基迁移，因此放弃了通过手性HPLC分离对映体的方法，并进行了总的手性合成。在化学合成之前，通过分子构象分析预测了“正确的”对映体模板的选择，该构象分析将DAG的两种对映体的假定“活性”进行了比较。两个对映体内酯模板的构象。DAG的这种“活性”构象源自先前开发的药效团模型，该模型使用强力佛波二酯分子作为理想的刚性模板。该分析的结果表明“正确的”内酯模板对应于DAG的非活性（R）-异构体。该分析还预测对应于活性（S）-DAG对映异构体的内酯模板不能充分地适合药效基团。从共同的双环中间体（5R，8R，9R）-8
• Conformationally Constrained Analogues of Diacylglycerol. 13. Protein Kinase C Ligands Based on Templates Derived from 2,3-Dideoxy-<scp>l</scp>-<i>erythro(threo)</i>-hexono-1,4-lactone and 2-Deoxyapiolactone
  作者：Jeewoo Lee、Nancy E. Lewin、Peter Acs、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm960525v

  日期：1996.1.1

  In the present investigation, the last two possible modes of generating conformationally semirigid diacylglycerol (DAG) analogues embedded into five-membered ring lactones as templates III and IV are investigated. The first two templates studied in previous investigations corresponded to 2-deoxyribonolactone (template I) and 4,4-disubstituted gamma-butyrolactone (template II), with the latter producing potent protein kinase C (PK-C) ligands with low nanomolar binding affinities. The templates reported in this work correspond to 2,3-dideoxy-L-erythro- or -threo-hexono-1,4-lactone (template III) and 2-deoxyapiolactone (template IV). Compounds constructed with the dideoxy-L-erythro- or -threo-hexono-1,4-lactone template were synthesized stereospecifically from tri-O-acetyl-L-glucal and L-galactono-1,4-lactone, respectively. Compounds constructed with the 2-deoxyapiolactone template were synthesized stereoselectively from di-O-isopropylidene-alpha-D-apiose. Inhibition of the binding of [H-3]phorbol-12,13-dibutyrate to PK-C alpha showed that only the threo-isomer, 5-O-tetradecanoyl-2,3-dideoxy-L-threo-hexono-1,4-lactone (2) was a good PK-C ligand (K-i = 1 mu M). The rest of the ligands had poorer affinities with K-i values between 10 and 28 mu M. With these results, the order of importance of five-membered ring lactones as competent templates for the construction of semirigid DAG surrogates with effective PK-C binding affinity can be established as II much greater than I similar to III > IV.
• Methyl 3-formyl-2,3-O-isopropylidene-D-erythrofuranoside (D-apiose aldal) and derivatives
  作者：Ronald J. Nachman、Michael Hoenel、Theresa M. Williams、R. Christopher Halaska、Harry S. Mosher

  DOI：10.1021/jo00375a010

  日期：1986.12