(3aR,4R,6R,6aR)-6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol | 33823-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4R,6R,6aR)-6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• 英文别名: 2,3:5,6-di-O-isopropylidene-D-mannofuranose；(3aR,6R,6aR)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• CAS: 33823-04-0
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: JWWCLCNPTZHVLF-WWGUJXLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,4R,6R,6aR)-6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol 在 4-二甲氨基吡啶 、 sodium sulfide 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (3aR,4S,6aS)-4-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole
  参考文献：
  名称：

  Discovery of a New Nucleoside Template for Human A₃ Adenosine Receptor Ligands:  d-4‘-Thioadenosine Derivatives without 4‘-Hydroxymethyl Group as Highly Potent and Selective Antagonists

  摘要：

  Truncated D-4'-thioadenosine derivatives lacking the 4'-hydroxymethylene moiety were synthesized starting from D-mannose, using cyclization to the 4-thiosugar and one-step conversion of the diol to the acetate as key steps. At the human A(3) adenosine receptor (AR), N(6)-substituted purine analogues bound potently and selectively and acted as antagonists in a cyclic AMP functional assay. An N(6)-(3-chlorobenzyl)purine analogue 9b displayed a K(i) value of 1.66 nM at the human A(3) AR. Thus, truncated D-4'-thioadenosine is an excellent template for the design of novel A(3) AR antagonists to act at both human and murine species.

  DOI：

  10.1021/jm070259t
• 作为产物：
  描述：

  (3aR,4R,6aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-pent-4-enyloxy-tetrahydro-furo[3,4-d][1,3]dioxole 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 乙腈 为溶剂， 以75%的产率得到(3aR,4R,6R,6aR)-6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol
  参考文献：
  名称：

  由双丙酮葡萄糖正式合成羟基脂肪酸

  摘要：

  描述了1和2的立体选择性合成。分别存在于1和2中的邻二醇体系（12R，13S）和（12S，13S）已从双丙酮葡萄糖的C-3，C-4转移。

  DOI：

  10.1016/s0040-4039(00)74213-4

文献信息

• A convenient method for deuteration at the alpha position of an oxo group in carbohydrates
  作者：Ahmed El Nemr、Tsutomu Tsuchiya

  DOI：10.1016/s0040-4039(98)00539-5

  日期：1998.5

  CH-Hydrogens at the alpha position of an oxo group in carbohydrates are readily exchanged in 4:4:2:3 1,4-dioxane-THF-Et3N-D2O.

  碳水化合物中一个羰基的α位上的CH-氢很容易在4：4：2：3 1,4-二恶烷-THF-Et 3 N-D 2 O中交换。
• Synthesis of Chiral Spiroacetals from Carbohydrates
  作者：Angeles Martín、José A. Salazar、Ernesto Suárez

  DOI：10.1021/jo960060g

  日期：1996.1.1

  Chiral spiroacetals of the 1,7-dioxaspiro[5.5]undecane, 1,6-dioxaspiro[4.5]decane, and 1,6-dioxaspiro[4.4]nonane types have been prepared from carbohydrates in pyranose or furanose forms. The spirocyclization reaction has been accomplished from a conveniently homologated carbohydrate by an intramolecular hydrogen abstraction reaction promoted by alkoxy radicals. Thus, 2,3,4,6-tetra-O-benzyl-1-deox

  由吡喃糖或呋喃糖形式的碳水化合物制备了1,7-二氧杂螺[5.5]十一烷，1,6-二氧杂螺[4.5]癸烷和1,6-二氧杂螺[4.4]壬烷类型的手性螺缩醛。螺环化反应已经通过由烷氧基自由基促进的分子内氢提取反应，从便利地同源的碳水化合物完成。因此，在（二乙酰氧基碘）苯存在下，用可见光光解2,3,4,6-四-O-苄基-1-脱氧-1-（3'-羟丙基）-α-D-吡喃葡萄糖（2）。和碘制得（1R）-（3）和（1S）-2,3,4,6-四-O-苄基-1-脱氧-D-吡喃葡萄糖-1-螺-2'-四氢呋喃的混合物（ 4）。甲基6-脱氧-6-（2'-羟乙基）-2,3,4-三-O-甲基-α-D-吡喃葡萄糖苷（8）的光解得到异构的螺缩醛甲基（5S）-（9）和（5R）-6-脱氧-5,2'-环氧-6-乙基-2,3，4-螺-O-甲基-α-D-吡喃葡萄糖苷（10）的螺中心现在位于C-5。[5.5]十一烷系列的螺缩醛：甲基（5R）-（19）和（5S）-6-脱氧-5
• Chiral Cyclobutanols and Cyclopentane Dimers via Samarium(II) Iodide Induced Keto-Olefin Cyclisations of Carbohydrate-Derived Unsaturated Ketones
  作者：D. Williams、Judy Caddy、Kevin Blann、J. Grové、Cedric Holzapfel

  DOI：10.1055/s-0029-1216824

  日期：2009.6

  Some pentose and hexose sugars were converted into unsaturated ketone derivatives, which themselves served as substrates for 4-exo-trig radical cyclisation reactions mediated by SmI2. Depending on the order of addition of reagents, the keto-olefins could also be made to undergo a surprising tandem 5-endo-trig cyclisation/dimerisation reaction to a cyclopentane dimer or a cyclobutane monomer. carbocycles

  一些戊糖和己糖被转化为不饱和酮衍生物，它们本身可作为SmI 2介导的4- exo - trig自由基环化反应的底物。取决于试剂的添加顺序，还可以使酮-烯烃进行令人惊奇的串联5-内-三-trig环化/二聚反应，形成环戊烷二聚体或环丁烷单体。 碳环-碳水化合物-自由基反应-mar-闭环
• De‐epimerization of Monosaccharides by Dynamic Kinetic Resolution: Ligand‐Controlled Synthesis of <i>O</i>‐Aryl‐Glycosides through Copper‐Catalyzed Cross‐Coupling
  作者：Tian‐Yang Liu Hou、Yi‐Xian Li、Yue‐Mei Jia、Chu‐Yi Yu

  DOI：10.1002/adsc.202300997

  日期：2024.3.8

  We report a strategy for stereoselective O-aryl-glycoside synthesis by copper-catalyzed cross-coupling of a variety of anomeric sugars and (hetero)aromatic iodides. Stereocontrol of the α/β selectivity can be successfully realized by slight structural modifications of the oxalic diamide ligands. Mechanistic studies indicated a dynamic kinetic resolution (DKR) reaction mechanism controlled by the ligand

  我们报告了一种通过铜催化交叉偶联各种异头糖和（杂）芳香族碘化物来立体选择性 O-芳基糖苷合成的策略。通过草酸二酰胺配体的轻微结构修饰可以成功实现α/β选择性的立体控制。机理研究表明了由配体结构控制的动态动力学拆分（DKR）反应机制。该反应可以在克级进行，并且也已应用于一些天然产物的合成。
• Acetonides of α-hydroxy-δ-altronolactones
  作者：Claire J.F. Bichard、Antony J. Fairbanks、George W.J. Fleet、Nigel G. Ramsden、Klaus Vogt、Orla Doherty、Lisa Pearce、David J. Watkin

  DOI：10.1016/s0957-4166(00)82202-8

  日期：1991.1

  The preparation and characterisation of some derivatives of alpha-hydroxy-delta-lactones, in which the delta-carbon substituent on the lactone ring is trans to an adjacent isopropylidene protected diol, are described; the X-ray crystal structures of 3,4-O-isopropylidene-D-altrono-1,5-lactone and of 3,4:6,7-di-O-isopropylidene-D-glycero-D-altro-heptono-1,5-lactone are reported.