(2E)-4,5,6-tri-O-acetyl-2,3-dideoxy-aldehydo-D-erythro-hex-2-enose | 37793-29-6

• 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: (2E)-4,5,6-tri-O-acetyl-2,3-dideoxy-aldehydo-D-erythro-hex-2-enose
• 英文别名: (2E)-4,5,6-tri-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enose；(2E,4S,5R)-4,5,6-triacetoxy-2-hexenal；(e)-4,5,6-tri-O-acetyl-2,3-dideoxy-d-erythro-hex-2-enose；[(E,2R,3S)-2,3-diacetyloxy-6-oxohex-4-enyl] acetate
• CAS: 37793-29-6
• 化学式: C₁₂H₁₆O₇
• 分子量: 272.255
• InChiKey: ZHPSKMIKFZDFJM-RUULKOMLSA-N

物化性质

• 沸点：
  319.9±21.0 °C(Predicted)
• 密度：
  1.190±0.06 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：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2E)-4,5,6-tri-O-acetyl-2,3-dideoxy-aldehydo-D-erythro-hex-2-enose 在 吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 sodium methylate 、 氢气 作用下， 生成 (2R,3S,E)-3,6-bis(tetrahydropyranyloxy)-4-hexen-2-ol
  参考文献：
  名称：

  Noshita, Toshiro; Sugiyama, Takeyoshi; Yamashita, Kyohei, Agricultural and Biological Chemistry, 1991, vol. 55, # 4, p. 1207 - 1209

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,2R,3R)-1-((4R,5R)-5-acetoxy-2,2-dimethyl-1,3-dioxolan-4-yl)butane-1,2,3,4-tetrayl tetraacetate 生成 (2E)-4,5,6-tri-O-acetyl-2,3-dideoxy-aldehydo-D-erythro-hex-2-enose
  参考文献：
  名称：

  Conversion of Penta-O-Acetyl-1,2-O-isopropylidene-aldehydo-D-glucose into Tri-O-acetyl-2,3-dideoxy-aldehydo-D-erythro-hex-2-enose.

  摘要：

  DOI：

  10.3891/acta.chem.scand.28b-0853

文献信息

• A Two-Carbon Homologation of Aldehydes and Ketones Using Ynamides
  作者：Richard Hsung、Lingfeng You、Ziyad Al-Rashid、Ruth Figueroa、Sunil Ghosh、Gang Li、Ting Lu

  DOI：10.1055/s-2007-984513

  日期：2007.7

  Reactions of ynamides with Lewis acid activated -aldehydes, enals, or ketones in the formation of acrylic amides are described here. The overall process is an equivalent of a two-carbon homologation of aldehydes or ketones and is selective for the E-isomer.

  在此描述了炔酰胺与路易斯酸活化的醛、烯醛或酮在丙烯酰胺形成中的反应。整个过程相当于醛或酮的双碳同系化，并且对 E 异构体具有选择性。
• Higher acyclic nitrogen containing deoxy sugar derivatives: A new lead in the generation of antimycobacterial chemotherapeutics
  作者：R Pathak

  DOI：10.1016/s0968-0896(02)00045-7

  日期：2002.6

  Syntheses of higher acyclic nitrogen containing deoxy sugar derivatives via nitroaldol reaction of different nitroalkanes with 2,3-dideoxy-alpha,beta-unsaturated aldehydo sugars obtained from glycals namely acetylated glucal and galactal and their in vitro antimycobacterial activity are presented.

  提出了通过不同硝基烷烃与2,3-二脱氧-α，β-不饱和醛糖的硝基羟醛的硝基醛缩合反应合成高级无环含氮脱氧糖衍生物的方法及其体外抗分枝杆菌活性。
• Aza- and carbo-[3+3] annulations of exo-cyclic vinylogous amides and urethanes. Synthesis of tetrahydroindolizidines and an unexpected formation of hexahydroquinolines
  作者：Sunil K. Ghosh、Grant S. Buchanan、Quincy A. Long、Yonggang Wei、Ziyad F. Al-Rashid、Heather M. Sklenicka、Richard P. Hsung

  DOI：10.1016/j.tet.2007.09.089

  日期：2008.1

  Annulations of exo-cyclic vinylogous amides and urethanes with vinyl iminium salts are described here. We observed an intriguing dichotomy in their reaction pathways. For pyrrolidine- and azepane-based vinylogous amides or urethanes, aza-[3+3] annulation would dominate to give tetrahydroindolizidines, whereas, unexpectedly, for piperidine-based vinylogous amides or urethanes, carbo-[3+3] annulation was

  这里描述了外环插烯酰胺和氨基甲酸酯与乙烯基亚胺盐的[3+3]环化。我们观察到它们的反应途径中存在有趣的二分法。对于基于吡咯烷和氮杂环庚烷的插烯酰胺或氨基甲酸酯，氮杂-[3+3]环化将主导产生四氢吲哚里西啶，而出乎意料的是，对于基于哌啶的插烯酰胺或氨基甲酸酯，碳-[3+3]环化是途径，产生六氢喹啉。这种对比的起源可能与初始反应途径在 C-1,2-加成和 C-1,4-加成之间的转换有关。
• Studies on epoxidation of enantiomerically pure 2,3-dideoxy hex-2-enitols: a convenient access to highly functionalized enantiomerically pure tetrahydrofuran derivatives
  作者：Ram Sagar、L. Vijaya Raghava Reddy、Arun K. Shaw

  DOI：10.1016/j.tetasy.2006.04.022

  日期：2006.4

  8–14 derived from their respective glycals with Sharpless, m-CPBA and Camp’s reagents was carried out in order to obtain 2,3-epoxy alcohols keeping in view the versatility of these synthons in synthetic chemistry for the preparation of various molecules of biological importance by suitable chemical transformations. During the course of this study, the Sharpless asymmetric epoxidation reaction was found

  上对映体纯的烯丙醇的环氧化的详细比较研究8 - 14从与夏普勒斯，其各自衍生烯糖米-CPBA和坎普的试剂是为了获得2,3-环氧醇鉴于保持这些合成子的通用性进行在合成化学中用于通过合适的化学转化制备具有生物学重要性的各种分子。在该研究过程中，由于其温和的反应条件，Sharpsless不对称环氧化反应被发现是一种空前的替代方法，用于合成高度官能化的对映体纯的四氢呋喃衍生物。还研究了它们形成的详细机理。
• Tandem β-Elimination-Morita-Baylis-Hillman Reaction in α,β-Unsaturated Sugar Aldehydes
  作者：Pilar Areces、Joaquín Plumet、Esther Carrasco、Alicia Mancha

  DOI：10.1055/s-2006-926366

  日期：——

  The first Morita-Baylis-Hillman reaction of a 1-formylbutadiene derivative is reported. In addition, a convenient synthesis of 2-acetoxy-4-formylbutadiene derivatives starting from easily available D-galactal and D-arabinal is also described.

  报道了 1-甲酰基丁二烯衍生物的第一次 Morita-Baylis-Hillman 反应。此外，还描述了从容易获得的 D-半乳醛和 D-阿拉伯醛开始方便地合成 2-acetoxy-4-formylbutadiene 衍生物。