2-脱氧-b-D-吡喃核糖 | 22900-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: 2-脱氧-b-D-吡喃核糖
• 英文名称: 2-deoxy-β-D-erythro-pentopyranose
• 英文别名: 2-deoxy-D-ribose；2-Deoxy-beta-D-ribopyranose；(2R,4S,5R)-oxane-2,4,5-triol
• CAS: 22900-10-3
• 化学式: C₅H₁₀O₄
• 分子量: 134.132
• InChiKey: ZVQAVWAHRUNNPG-VPENINKCSA-N

物化性质

• 沸点：
  332.1±42.0 °C(Predicted)
• 密度：
  1.516±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-脱氧-b-D-吡喃核糖 在 diclazuril 作用下， 以 重水 为溶剂， 生成 2-脱氧-D-核糖
  参考文献：
  名称：

  Bauer, Hans; Brinkmeier, Arno; Buddrus, Joachim, Liebigs Annalen der Chemie, 1986, # 10, p. 1804 - 1808

  摘要：

  DOI：
• 作为产物：
  描述：

  allyl vinylacetate 在 K₂Os(OH)4 titanium(IV) isopropylate 、 potassium dihydrogenphosphate 、 Hydroquinone 1,4-phthalazinediyl diether 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 23.5h， 生成 2-脱氧-b-D-吡喃核糖
  参考文献：
  名称：

  Synthesis of 2,6-Dideoxysugars via Ring-Closing Olefinic Metathesis

  摘要：

  graphicGrubbs' RuCl2(=CHPh)(PCy3)(2) (catalyst 1) and RuCl2(=CHPh)(PCy3)(IMess) (catalyst 2) complexes have been successfully utilized in the construction of beta,gamma-unsaturated delta-lactones containing various substitution patterns of methyl groups. Asymmetric dihydroxylation followed by reduction leads to 3,4-cis-dihydroxy-2,6-dideoxypyranoses, which have proven to play very important biological roles as key components of natural products.

  DOI：

  10.1021/ol026710m

文献信息

• Stereocontrolled Synthesis of a Possible Stereoisomer of Laurenidificin and a Formal Total Synthesis of (+)-Aplysiallene Featuring a Stereospecific Ring Contraction
  作者：Shoji Kobayashi、Taiki Yokoi、Tomoharu Inoue、Yutaka Hori、Tomoaki Saka、Taiki Shimomura、Araki Masuyama

  DOI：10.1021/acs.joc.5b02595

  日期：2016.2.19

  We report a highly stereocontrolled total synthesis of one of the possible stereoisomers of laurenidificin. Highlights of the synthesis include the formation of the 2,6-dioxabicyclo[3.3.0]octane framework by a stereospecific bromolactonization−α-bromination–ring contraction sequence, followed by a stereoselective propargylation, an insertion of the Z-enyne side chain by a hydroindation/cross coupling

  我们报告了一个可能的立体异构的月桂烯苷的高度立体控制的全合成。合成的亮点包括通过立体定向的溴化-α-溴化-环收缩序列形成2，6-二氧杂双环[3.3.0]辛烷骨架，然后进行立体选择性的炔丙基化，Z-烯炔侧链的插入加氢indindation /交叉偶合反应，并在13℃下用有机铜酸盐试剂进行乙基化。虽然合成化合物与天然产物不完全相同，但根据NMR分析提出了天然产物的绝对立体化学。此外，通过扩展环收缩策略，实现了（+）-aplysiallene的正式全合成。
• Detection of 2-Deoxy-<scp>D</scp>-ribose Radicals Generated by the Reaction with the Hydroxyl Radical using a Rapid Flow-ESR Method
  作者：Yasunori OHASHI、Hisashi YOSHIOKA、Hiroe YOSHIOKA

  DOI：10.1271/bbb.66.847

  日期：2002.1

  ESR spectrum of the short-lived radicals derived from 2-deoxy-D-ribose by the reaction with the hydroxyl radical (HO*) was measured using a rapid flow method. A dielectric mixing resonator was used for the measurement, which made it possible to measure the highly sensitive ESR spectra of the radicals with a lifetime of the order of milliseconds. A complex spectrum was obtained and the spectral simulation

  使用快速流动法测量通过与羟基自由基（HO *）反应衍生自2-脱氧-D-核糖的短寿命自由基的ESR光谱。使用介电混合谐振器进行测量，这使得可以以几毫秒的寿命测量自由基的高度敏感的ESR光谱。获得了一个复杂的光谱，并进行了光谱模拟，以表明这是由于五个自由基（IV）引起的信号叠加。它们中的三个是通过在2-脱氧-D-核糖分子的C-1（I），C-3（II）和C-4（III）位置处的HO *脱氢而形成的那些。其他两个（IV和V）是通过消除III和II中的水分子而形成的羰基共轭基团。
• A Rapid Synthesis of Pyranoid Glycals from Glycosyl Bromides
  作者：Cullen L. Cavallaro、Jeffrey Schwartz

  DOI：10.1021/jo00126a075

  日期：1995.10
• Richards, Journal of the Chemical Society, 1954, p. 3638
  作者：Richards

  DOI：——

  日期：——
• The oxygen-18 isotope shift in carbon-13 NMR spectroscopy. 14. Kinetics of oxygen exchange at the anomeric carbon of D-ribose and D-2-deoxyribose
  作者：Sergio J. Cortes、Tony L. Mega、Robert L. Van Etten

  DOI：10.1021/jo00003a009

  日期：1991.2

  The kinetics of the oxygen-exchange reaction at the anomeric carbon atoms of D-ribose and D-2-deoxyribose (2-deoxy-D-erythro-pentose) were compared using the O-18 isotope induced shift in C-13 NMR spectroscopy. Measurements were made at a number of temperature and pH values. The oxygen-exchange reaction for these sugars is strongly pH-dependent, displaying regions of acid, water, and base catalysis. At 25-degrees-C the oxygen-exchange rate of D-ribose was found to be approximately 20-fold greater than the rate for D-glucose between pH 2 and 9. In turn, the oxygen-exchange rate for D-2-deoxyribose was greater than the rate for D-ribose by approximately 5-fold above pH 4 and by greater than 10-fold below pH 4. The results are analyzed in terms of steric and inductive effects on the hydration kinetics of the open-chain forms and by comparison with the hydration reaction of simple aldehydes. The study also includes quantitative data, based upon C-13 NMR line intensities, for the various anomeric forms that exist in solutions of these sugars at the different temperature and pH values used in the kinetic measurements reported here. In each case, the oxygen-exchange reactions of the anomers are slow relative to the rate of anomerization, so that the anomers appear to exchange oxygen at the same rate.