2-deoxy-D-ribose | 36792-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-deoxy-D-ribose
• 英文别名: 2-Deoxy-alpha-D-ribopyranose；(2S,4S,5R)-oxane-2,4,5-triol
• CAS: 36792-85-5
• 化学式: C₅H₁₀O₄
• 分子量: 134.132
• InChiKey: ZVQAVWAHRUNNPG-LMVFSUKVSA-N

物化性质

• 熔点：
  91.0 °C

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

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2-deoxy-D-ribose 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-deoxy-D-ribose
  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

• Quantitative analysis of selective glycosylation of saccharides with aromatic amines
  作者：Toshihiko Hanai、Keiko Shimada、Nobuhiro Koyama、Yukio Nohara

  DOI：10.1016/j.carres.2020.108171

  日期：2020.12

  Glycosylation, a part of the Maillard reaction, occurs non-enzymatically in food and biological processes. The selectivity of N-glycosylation was analyzed based on the reactivity of monosaccharides with aromatic amines, including aromatic amino acids, and the degree of molecular interaction (MI) measured using liquid chromatography. Furthermore, the chemical structures of reaction products were determined

  糖基化是美拉德反应的一部分，在食品和生物过程中以非酶促方式发生。N-糖基化的选择性基于单糖与芳香胺（包括芳香氨基酸）的反应性以及使用液相色谱测量的分子相互作用 (MI) 程度进行分析。此外，使用 X 射线晶体学和/或 NMR 确定反应产物的化学结构。使用不同构象的优化能量值在计算机中估计可能的反应产物。使用模型相的计算机分析计算氨基和糖类的 MI 能量值。具有较大 MI 值的糖类容易产生稳定的 N-糖苷晶体。葡萄糖（一种能量糖）的反应速度很慢，它很容易产生 Amadori 化合物。芳香胺与糖类反应性的研究、单糖在色谱中氨基相保留的测量以及 N-糖苷的合成以确定其结构将为候选药物的修饰提供有关选择性糖基化的有用信息以提高它们的水溶性。
• Process for production 2-deoxyaldose compound
  申请人：Umetani Hideki

  公开号：US20060069289A1

  公开（公告）日：2006-03-30

  A method for preparing 2-deoxyaldoses on an industrial scale in which the yield or the volumetric efficiency is excellent and the operation is simple, as compared to the conventionally known preparation method. In one aspect, a compound represented by a defined formula, such as 2-keto-3-deoxygluconic acid or the like, is reduced by the catalytic hydrogenation method using a metal, such as palladium or the like, or a compound such as 2-keto-3-deoxygluconic acid or the like is reduced by using a hydride reducing agent in a solvent of not more than 30 weight times the amount of the above compound, for synthesizing 2-keto-3-deoxyaldonic acid. The 2-keto-deoxyaldonic acid is decarboxylated to obtain 2-deoxyaldoses.

  一种制备2-脱氧醛糖的工业规模方法，其中产率或体积效率优异且操作简单，与传统已知的制备方法相比。在其中一个方面，使用金属（例如钯或类似物）或化合物（例如2-酮-3-脱氧葡萄糖酸或类似物）的催化氢化方法还原由定义的公式表示的化合物，或使用不超过上述化合物量的30倍的溶剂使用氢化还原剂还原化合物（例如2-酮-3-脱氧葡萄糖酸或类似物），以合成2-酮-3-脱氧醛酸。2-酮-脱氧醛酸脱羧化可获得2-脱氧醛糖。
• Synthetic studies on palytoxin. Stereocontrolled, practical synthesis of the C.101–C.115 segment
  作者：Soo Sung Ko、Larry L Klein、Klaus-Peter Pfaff、Yoshito Kishi

  DOI：10.1016/s0040-4039(00)85616-6

  日期：1982.1

  A stereocontrolled and practical synthetic route to the acetal 2a, a degradation product of palytoxin, in optically active form is described.

  描述了一种立体控制的，实用的合成途径，即光学活性形式的乙缩醛2a（一种palytoxin的降解产物）。
• <scp>C‐Aryl</scp> Glycosylation via Interrupted Pummerer Rearrangement^†
  作者：Jiagen Li、Xuefeng Jiang

  DOI：10.1002/cjoc.202300308

  日期：2023.11

  enzymes. Herein, C-aryl glycosylation was established for the synthesis of 2-sulfur C-aryl glycals and 1,2-dihydrobenzofuran-fused C-aryl glycosides via interrupted Pummerer process, featured with sulfonium-tethered [3,3]-sigmatropic rearrangement between sulfoxide glycals and phenols. This protocol offers a broad substrate scope with diverse glycosyl and phenols. Dapagliflozin, Empagliflozin, and Ipragliflozin

  C-芳基糖苷由于其独特的抗酶水解特性，是药物发现中重要的碳水化合物衍生物。在此，建立了通过间断Pummerer法合成2-硫C-芳基糖醛和1,2-二氢苯并呋喃稠合C-芳基糖苷的C-芳基糖基化，其特征在于锍系链的[3,3 ] -σ重排亚砜糖醛和酚类。该实验方案提供了具有多种糖基和酚类的广泛底物范围。达格列净、恩格列净和伊格列净类似物分别是直接实现的。
• 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.