3'-O-acetyl-1',2'-O-isopropylidene-α-D-ribo-pentoaldo-1',4'-furanose | 24807-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'-O-acetyl-1',2'-O-isopropylidene-α-D-ribo-pentoaldo-1',4'-furanose
• 英文别名: [(3aR,5S,6R,6aR)-5-formyl-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate
• CAS: 24807-97-4
• 化学式: C₁₀H₁₄O₆
• 分子量: 230.218
• InChiKey: ALUIPQFDFUTPRV-FNCVBFRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-O-acetyl-1',2'-O-isopropylidene-α-D-ribo-pentoaldo-1',4'-furanose 在 potassium permanganate 、 溶剂黄146 作用下， 反应 6.0h， 以3.08 g的产率得到3-O-acetyl-1,2-O-isopropylidene-α-D-ribofuranuronic acid
  参考文献：
  名称：

  Synthesis of N-methyl-d-ribopyranuronamide nucleosides

  摘要：

  The Synthesis of N-methyl-D-ribopyranuronamide nucleosides is described. The key route is the rearrangement of a 1,2-O-isopropylidene protected furanose sugar with a carboxamide function in the 4-position to a ribopyranuronamide ring. The Lewis acid catalyzed condensation of adenine and thymine nucleobases with the per-O-acetylated N-methyl-D-ribopyranuronamide sugar is used to give the target nucleosides as a mixture of the alpha and beta anomers. The mixture was separated and the final Compounds were obtained by deacetylation in basic conditions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.027
• 作为产物：
  描述：

  在 4,4'-bis(dichloroiodo)biphenyl 、 四乙基溴化铵 作用下， 以 氯仿 为溶剂， 反应 0.75h， 以35%的产率得到3'-O-acetyl-1',2'-O-isopropylidene-α-D-ribo-pentoaldo-1',4'-furanose
  参考文献：
  名称：

  Mild and Recyclable Hypervalent Iodine System for Oxidation of Alcohols

  摘要：

  DOI：

  10.1080/00397910600978242

文献信息

• Polymeric enzyme mimics: catalytic activity of ribose-containing polymers for a phosphate substrate
  作者：Man Jung Han、Kyung Soo Yoo、Young Heui Kim、Ji Young Chang

  DOI：10.1039/b301166f

  日期：——

  catalytic activity was attributable to the vic-cis-diols of riboses on polymer chains, which formed hydrogen bonds with two phosphoryl oxygen atoms of phosphates so as to activate the phosphorus atoms to be attacked by nucleophiles. The catalytic activity was negligible for polymer 11 where vic-cis-diol groups were blocked with isopropylidene groups. The catalytic activity was attributable to the vic-cis-diols

  含有核糖环的聚合物：聚（5'-丙烯酰胺基-5'-脱氧-1'，2'-O-异亚丙基-α-D-核糖）（11），聚（5'-丙烯酰胺基-5'-脱氧-制备α-D-核糖）（12）和聚（5'-丙烯酰胺基-5'-脱氧-1'-O-甲基-D-核糖）（13）作为酶模拟物。具有游离vic-cis-二醇基团的聚合物12和13催化磷酸二酯（乙基对硝基苯基磷酸酯和N-甲基吡啶鎓4-叔丁基邻苯二酚环状磷酸酯）和磷酸单酯底物的水解，其加速速率为10约等于10（3 ）与未催化的反应相比。他们还催化了逆反应，即磷酸单酯被酯化为磷酸二酯，以及醇被磷酸根离子磷酸化。催化活性归因于聚合物链上核糖的vic-cis-二醇，它与磷酸盐的两个磷酰基氧原子形成氢键，从而激活磷原子，使其受到亲核试剂的攻击。聚合物11的催化活性可忽略不计，其中vic-顺-二醇基被异丙叉基封端。催化活性归因于聚合物链上核糖的vic-顺式-二醇，其与磷酸的两个磷酰氧原
• Orientation of the Addition of Dimethyl Phosphonate to 5,6-Dideoxy-6-nitro-D-hex-5-enofuranoses
  作者：Tadashi Hanaya、Hiroshi Yamamoto、Hiroshi Yamamoto

  DOI：10.1246/bcsj.65.1154

  日期：1992.4

  The addition of dimethyl phosphonate to six 5,6-dideoxy-6-nitro-D-hex-5-enofuranoses at 25 °C in the presence of triethylamine preponderantly gave (5R)-adducts, whereas the same reaction at 100 °C without a base yielded (5S)-adducts as the main products.

  在三乙胺存在下，在 25 °C 下将膦酸二甲酯添加到六个 5,6-二脱氧-6-硝基-D-己基-5-烯呋喃糖中，主要产生 (5R)-加合物，而在 100 °C 下的反应相同a 碱以 (5S)-加合物为主要产物。
• The catalytic activity of ribose-containing polymers for the hydrolysis of phosphodiester and the cleavage of nucleic acid
  作者：Man Jung Han、Kyung Soo Yoo、Young Heui Kim、Ji Young Chang

  DOI：10.1016/s0040-4039(02)01123-1

  日期：2002.8

  In order to investigate the catalytic activity for the hydrolysis of phosphodiester and the cleavage of nucleic acids, ribose-containing polymers 11, 12 and 13 were synthesized. While polymer 11 showed no catalytic activity, polymers 12 and 13 catalyzed the cleavage of nucleic acids and the hydrolysis of a phosphodiester substrate. The catalytic activity was attributable to the vic-cis diols of riboses

  为了研究对于磷酸二酯的水解和核酸的裂解的催化活性，聚合物含有核糖11，12和13进行合成。尽管聚合物11没有催化活性，但是聚合物12和13催化核酸的裂解和磷酸二酯底物的水解。催化活性为可归因于VIC -顺式上的聚合物链，其形成的氢键与磷酸盐的两种磷酸氧原子，从而激活磷原子的核糖的二醇被亲核试剂攻击（H 2 O）。