tri-O-acetyl-D-arabono-1,4-lactone | 16751-37-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tri-O-acetyl-D-arabono-1,4-lactone
• 英文别名: 2,3,5-tri-O-acetyl-D-arabino-1,4-lactone；2,3,5-Tri-O-acetyl-D-arabino-1,4-lacton；O²,O³,O⁵-triacetyl-D-arabinonic acid-lactone；O²,O³,O⁵-Triacetyl-D-arabinonsaeure-lacton；2,3,5-Tri-O-acetyl-D-arabinonic acid, gamma-lactone；[(2R,3R,4S)-3,4-diacetyloxy-5-oxooxolan-2-yl]methyl acetate
• CAS: 16751-37-4
• 化学式: C₁₁H₁₄O₈
• 分子量: 274.227
• InChiKey: JIILXWRHIYAEQM-BBBLOLIVSA-N

物化性质

• 沸点：
  309.2±31.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tri-O-acetyl-D-arabono-1,4-lactone 在 palladium on activated charcoal 氢氧化钾 、 diisoamyl borane 、 氢气 、 三乙胺 、 乙酰氯 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、10.13 MPa 条件下， 反应 25.0h， 生成 methyl 3-deoxy-α-D-threo-pentofuranoside
  参考文献：
  名称：

  Bock, Klaus; Lundt, Inge; Pedersen, Christian, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1981, vol. 35, # 3, p. 155 - 162

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4-Tri-O-acetyl-1-bromo-D-arabinopyranosyl cyanide 以33%的产率得到
  参考文献：
  名称：

  SOMSAK, LASZLO;PAPP, ETELKA;BATTA, GYULA;FARKAS, ISTVAN, CARBOHYDR. RES., 211,(1991) N, C. 173-178

  摘要：

  DOI：

文献信息

• Highly (<i>Z</i>)-Diastereoselective Synthesis of Trifluoromethylated <i>exo</i>-Glycals via Photoredox and Copper Catalysis
  作者：Christophe J.-M. Frédéric、Jérôme Cornil、Mathilde Vandamme、Lidia Dumitrescu、Abdellatif Tikad、Raphaël Robiette、Stéphane P. Vincent

  DOI：10.1021/acs.orglett.8b02891

  日期：2018.11.2

  Highly (Z)-diastereoselective approaches for the synthesis of trifluoromethylated exo-glycals by copper and photoredox catalysis are described. These complementary reactions are applicable to a wide range of methylene exo-glycals generated from the corresponding pyranoses and furanoses and give trifluoromethylated compounds under mild conditions in moderate to good yields. DFT calculations have allowed

  高度（Ž）用于合成三氟甲基化的方法-diastereoselective外型由铜和photoredox催化-glycals中描述。这些互补反应适用于由相应的吡喃糖和呋喃糖酶产生的各种亚甲基外糖，并在温和的条件下以中等至良好的收率得到三氟甲基化的化合物。DFT计算已使观察到的（Z）-立体选择性合理化。
• Metal-Catalyzed Organic Photoreactions. Iron(III)-Catalyzed Photoreactions of Aldo- and Ketohexoses
  作者：Shuji Ichikawa、Isao Tomita、Akira Hosaka、Tadashi Sato

  DOI：10.1246/bcsj.61.513

  日期：1988.2

  Under UV irradiation in the presence of iron(III) chloride or iron(III) triflate in pyridine, D-glucose, D-mannose, and D-galactose underwent a selective bond cleavage at the C1–C2 position, producing 4-O-formyl-D-arabinopyranose and 4-O-formyl-D-lyxopyranose. D-Fructose, under the same conditions, gave arabino-γ-lactone. The reaction was interpreted in terms of the photoinduced electron transfer within

  在存在于吡啶中的氯化铁 (III) 或三氟甲磺酸铁 (III) 的紫外线照射下，D-葡萄糖、D-甘露糖和 D-半乳糖在 C1-C2 位置发生选择性键裂解，产生 4-O-甲酰基-D-阿拉伯吡喃糖和4-O-甲酰基-D-吡喃吡喃糖。D-果糖，在相同条件下，得到阿拉伯-γ-内酯。该反应被解释为铁离子与碳水化合物分子螯合物内的光致电子转移。
• Stereocontrol in organic synthesis using silicon-containing compounds. Syntheses of (±)-2-deoxyribonolactone and (±)-arabonolactone
  作者：Ian Fleming、Sunil K. Ghosh

  DOI：10.1039/a804282i

  日期：——

  Samarium iodide reacts with methyl (Z)-3-dimethyl(4-methylphenyl)silylprop-2-enoate 5b to give dimethyl (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]hexane-1,6-dioate 8b with high stereoselectivity. This meso diester can be converted into (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]pentan-5-olide 16 by Dieckmann cyclisation, demethoxycarbonylation and Baeyer–Villiger reaction. Silyl-to-hydroxy

  碘化与（Z）-3-二甲基（4-甲基苯基）甲硅烷基丙-2-烯酸酯5b反应生成二甲基（3 RS，4 SR）-3,4-双[二甲基（4-甲基苯基）甲硅烷基]己烷-具有高立体选择性的1，6-二碘8b。通过Dieckmann环化，脱甲氧基羰基化和Baeyer-Villiger反应，该内消旋二酯可转化为（3 RS，4 SR）-3,4-双[二甲基（4-甲基苯基）甲硅烷基]戊基-5-乙交酯。甲硅烷基到羟基的转化和再内酯化得到（±）-脱氧核糖内酯，抗选择性烯醇盐羟基化，然后甲硅烷基到羟基的转化得到（±）-阿拉伯内酯。尝试合成具有相对构型的糖（3 RS，4 RS）被（3 RS，4 SR）-3,4-双[二[二甲基（4-甲基苯基）甲硅烷基] -5-羟基戊酸28- （3 RS，4 SR）-3,5-双[二甲基（4-甲基苯基）甲硅烷基]戊丹-1,4-乙交酯30。
• Stereoselective samarium(<scp>II</scp>)-induced coupling of β-silylacrylic esters: a synthesis of (±)-2-deoxyribonolactone
  作者：Ian Fleming、Sunil K. Ghosh

  DOI：10.1039/c39920001775

  日期：——

  Samarium iodide converts the β-silylacryalte 1c with high stereoselectivity into the racemic diester 2c, from which (±)-deoxyribonolactone 11 can be prepared.

  碘化钐将具有高立体选择性的β-甲硅烷基丙烯酸酯1c转化为外消旋二酯2c，由此可以制备(±)-脱氧核糖内酯11。
• 2,3-Anhydrosugars in Glycoside Bond Synthesis: Mechanism of 2-Deoxy-2-thioaryl Glycoside Formation
  作者：Dianjie Hou、Hashem A. Taha、Todd L. Lowary

  DOI：10.1021/ja9029945

  日期：2009.9.16

  A series of investigations probing the mechanism of the 2,3-anhydrosugar migration-glycosylation reaction were performed using a thioglycoside with the D-lyxo stereochemistry as the substrate. Among the work reported are the results of quantum mechanical calculations, NMR studies, the measurement of a-deuterium kinetic isotope effects, and the synthesis of a series of substrate analogues. All studies point to a consistent finding: that the reaction proceeds through an oxocarbenium ion intermediate, not an episulfonium ion as previously suggested. It is proposed that the high stereoselectivity of the reaction arises from a preferred "inside attack" of the nucleophile onto the oxocarbenium ion intermediate.