1,2,3-Tridesoxy-D-ribo-hept-1-enit | 58902-30-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,2,3-Tridesoxy-D-ribo-hept-1-enit
• 英文别名: D-ribo-1,2,3-trideoxy-hept-1-enitol；(2R,3S,4S)-hept-6-ene-1,2,3,4-tetrol
• CAS: 58902-30-0
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: UGFVKDFCBKARNH-XVMARJQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3-Tridesoxy-D-ribo-hept-1-enit 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 Anthracene-9-carboxylic acid (2R,3S,4S)-2,3,4-tris-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-hept-6-enyl ester
  参考文献：
  名称：

  无环1,2- / 1,3-混合戊醇。双色发激子耦合圆二色性光谱的合成及一般趋势

  摘要：

  描述了属于2 R对映体系列的无环1,2,3,4,6-戊醇的所有八个构型异构体的合成。这些戊醇的1-蒽基-2,3,4,6-对甲氧基肉桂酸酯在220–380 nm范围内产生独特的激子耦合圆二色光谱。与较低同源四元酚1-蒽基-2,3,4-对甲氧基肉桂酸酯的相应双色衍生物的CD的比较导致可预测的总体趋势，其中仅少量差异源自1,3- syn延伸，而主要差异产生从1,3-反扩展。

  DOI：

  10.1016/0040-4020(96)00012-9
• 作为产物：
  描述：

  1-(2',3',5'-Tri-O-benzyl-β-D-ribofuranosyl)ethin 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 生成 1,2,3-Tridesoxy-D-ribo-hept-1-enit
  参考文献：
  名称：

  Reduction of 2,3,5-tri-O-benzyl-α (and β)-d-ribofuranosylethyne

  摘要：

  DOI：

  10.1016/s0008-6215(00)85891-7

文献信息

• A stereochemically general synthesis of 2-deoxyhexoses via the asymmetric allylboration of 2,3-epoxy aldehydes
  作者：William R. Roush、Julie A. Straub、Michael S. VanNieuwenhze

  DOI：10.1021/jo00004a053

  日期：1991.2

  A stereochemically general strategy for the synthesis of 2-deoxyhexoses is described. This new approach involves the asymmetric allylboration of epoxy aldehydes 12 and 13, prepared via the Sharpless asymmetric epoxidation reaction, as a means of establishing the stereochemistry of the sugar backbone. Thus, the matched double asymmetric allylborations of 12 and 13 using tartrate allylboronates (R,R)- and (S,S)-7, respectively, provide erythro epoxy alcohols 14 and 16 with excellent diastereoselectivity ( > 96:4) and enantioselectivity (greater-than-or-equal-to 96% ee). The mismatched double asymmetric reactions of 12 and 13 using (S,S)- and (R,R)-7, respectively, provided the diastereomeric threo epoxy alcohols 15 and 17 with lower (ca. 75:25) but still synthetically useful selectivity. The enantiomeric purity of the major diastereomer in each of these reactions was determined to be greater than that of the epoxy aldehyde precursors. Epoxy alcohols 14 and 16 were converted with excellent selectivity to the l-arabino (21) and l-xylo (26) tetrols via neighboring group assisted alpha-substitution reactions of the derived phenylurethane derivatives 18 and 23. Stereochemically complementary beta-opening reactions were accomplished by treating primary alcohols 38, 40, 42, and 44 [prepared from 14-17, respectively, by ethoxyethylation of C(4)-OH and removal of the C(7)-tert-butyldiphenylsilyl (TBDPS) ethers] with NaOH in aqueous t-BuOH at reflux. Acid-catalyzed hydrolysis of the C(4)-ethoxyethyl ethers then provided tetrols d-35 (from 14), d-21 (from 15), d-30 (from 16), and d-26 (from 17), each with excellent stereoselectivity. These tetrols were isolated and fully characterized as the tetraacetate derivatives 36, 22, 31, and 27, respectively. These beta-opening reactions proceed by way of an epoxide migration (29 to 33) that inverts the stereochemistry at C(6) and activates C(7) toward nucleophilic attack. It is necessary that the C(4) hydroxyl be protected in three of the four stereoisomeric series to minimize competitive epoxide migration pathways (cf. 29 to 32a). arabino tetrol 21 and lyxo tetrol 30 were converted to 2-deoxyglucose and 2-deoxygalactose, respectively, by a standard ozonolytic sequence and then to 2-deoxyglucitol pentaacetate (45) and 2-deoxygalactitol pentaacetate (46) via NaBH4 reduction of the 2-deoxy sugars, thereby confirming all stereochemical assignments. The epoxide beta-opening technology was also applied to epoxy benzyl ether 47 (prepared from 14) and epoxy BOM ether 49 (deriving from 16). These reactions provide tetrol derivatives 48 and 50, respectively, in which the C(4)- and C(5)-hydroxyl functionality are suitably differentiated for use in subsequent synthetic sequences.
• Catalytic Enantioselective Isomerization of Silacyclopentene Oxides: New Strategy for Stereocontrolled Assembly of Acyclic Polyols
  作者：Dong Liu、Sergey A. Kozmin

  DOI：10.1002/1521-3773(20011217)40:24<4757::aid-anie4757>3.0.co;2-s

  日期：2001.12.17
• Acyclic 1,2-/1,3-mixed pentols. Synthesis and general trends in bichromophoric exciton coupled circular dichroic spectra
  作者：Dinesh Rele、Ning Zhao、Nakanishi Koji、Berova Nina

  DOI：10.1016/0040-4020(96)00012-9

  日期：1996.2

  The synthesis of all eight configurational isomers of acyclic 1,2,3,4,6-pentols belonging to the 2R enantiomeric series is described. The 1-anthroyl-2,3,4,6-p-methoxycinnamates of these pentols give rise to unique exciton coupled circular dichroic spectra in the range of 220–380 nm. Comparisons with the CD of corresponding bichromophoric derivatives of the lower homologous tetrols, 1-anthroyl-2,3,

  描述了属于2 R对映体系列的无环1,2,3,4,6-戊醇的所有八个构型异构体的合成。这些戊醇的1-蒽基-2,3,4,6-对甲氧基肉桂酸酯在220–380 nm范围内产生独特的激子耦合圆二色光谱。与较低同源四元酚1-蒽基-2,3,4-对甲氧基肉桂酸酯的相应双色衍生物的CD的比较导致可预测的总体趋势，其中仅少量差异源自1,3- syn延伸，而主要差异产生从1,3-反扩展。
• Reduction of 2,3,5-tri-O-benzyl-α (and β)-d-ribofuranosylethyne
  作者：J.Grant Buchanan、Alan R. Edgar、Michael J. Power、Gavin C. Williams

  DOI：10.1016/s0008-6215(00)85891-7

  日期：1975.12