1,2,3,5-tetra-O-acetyl-α-L-ribofuranose | 659722-55-1

• 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: 1,2,3,5-tetra-O-acetyl-α-L-ribofuranose
• 英文别名: 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose；Tetra-O-acetylribofuranose；α-1,2,3,5-tetra-O-acetyl-L-ribofuranose；[(2S,3S,4S,5S)-3,4,5-triacetyloxyoxolan-2-yl]methyl acetate
• CAS: 659722-55-1
• 化学式: C₁₃H₁₈O₉
• 分子量: 318.281
• InChiKey: IHNHAHWGVLXCCI-ZDEQEGDKSA-N

物化性质

• 沸点：
  385.6±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2,3,5-tetra-O-acetyl-α-L-ribofuranose 在 硫酸 作用下， 生成 C₉H₁₀O₉
  参考文献：
  名称：

  一种制备β-四乙酰-L-核糖的方法

  摘要：

  本发明提出了一种制备β‑四乙酰‑L‑核糖的方法，该制备方法以L‑核糖为起始原料，依次通过上甲基反应、上三个乙酰基反应、脱甲基反应、上第四个乙酰基反应得到粗Beta‑四乙酰‑L‑核糖糖浆；然后将制得的粗Beta‑四乙酰‑L‑核糖糖浆通过纯化处理得到精Beta‑四乙酰‑L‑核糖，该工艺工艺简单，成本低，且产率可达到51％‑55％。

  公开号：

  CN112300226A
• 作为产物：
  描述：

  L-呋喃核糖 在 硫酸 、 lithium carbonate 作用下， 反应 12.5h， 生成 1,2,3,5-tetra-O-acetyl-α-L-ribofuranose
  参考文献：
  名称：

  Synthesis of Methyl 1-(2,3,5-Tri-O-acetyl-β-l-ribofuranosyl)-1,2,4- triazole-3-carboxylate from l-Ribose:  From a Laboratory Procedure to a Manufacturing Process

  摘要：

  A two-step manufacturing process for methyl 1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate (1) was developed. In step 1, L-ribose was converted to a beta/alpha mixture of 1,2,3,5-tetra-O-acetyl-L-ribofuranoses (2 and 4). The step contained four chemical transformations and was completed in "one-pot" in approximately 95% yield. The crude step 1 product was reacted with methyl 1,2,4-triazole-3-carboxylate (3) in step 2 to produce 1. The successful utilization of both isomers (2 and 4) in step 2 offered advantages of higher overall yield and a much simplified process by eliminating the isolation of pure 2. The process was successfully scaled up to the pilot plant and subsequently in a manufacturing campaign using commercial production facilities.

  DOI：

  10.1021/op050051m

文献信息

• A stereospecific synthesis of l-deoxyribose, l-ribose and l-ribosides
  作者：Zhen-Dan Shi、Bing-Hui Yang、Yu-Lin Wu

  DOI：10.1016/s0040-4020(02)00230-2

  日期：2002.4

  inexpensive d-galactose from the chiral pool, l-deoxyribose, l-ribose and their derivatives were synthesized via mild reaction conditions. During the synthesis of l-deoxyribose, the key deoxygenation of the 2-hydroxy group of 3,5-O-dibenzyl-methyl-l-arabinofuranoside was performed by reduction of the corresponding triflate with tetrabutylammonium borohydride in high yield. During the synthesis of l-ribose, the

  使用来自手性库的廉价d-半乳糖，通过温和的反应条件合成了l-脱氧核糖，L-核糖 href=https://www.molaid.com/MS_126078 target="_blank">核糖及其衍生物。在1-脱氧核糖的合成过程中，通过高产率地用四丁基硼氢化铵还原相应的三氟甲磺酸酯，进行3，5- O-二苄基-甲基-1-阿拉伯呋喃糖苷的2-羟基的关键脱氧。在L-核糖的合成，2-羟基反演在同一衬底中的关键步骤是通过分子内小号进行Ñ 2串联反应。然后根据Vorbrüggen的条件对L-核糖基供体进行糖基化反应，得到L-核糖苷（L-尿苷，L-5-氟尿苷，L-碘尿苷，L-胸苷，L-吡啶，L-腺苷和L-鸟苷）高产。
• Process for producing a ribofuranose
  申请人：——

  公开号：US20040034213A1

  公开（公告）日：2004-02-19

  A method of converting pure &agr;-anomer or &bgr;/&agr;-anomer mixtures of 1,2,3,5-tetra-O-acetyl-L-ribofuranose to methyl-1-(2,3,5 -tri-O-acetyl-&bgr;-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate an intermediate for levovirin, as well as, the novel pure &agr;-anomer, alpha 1,2,3,5-tetra-O-acetyl-L-ribofuiranose, are useful in manufacturing levovirin.

  一种将纯的α-异构体或1,2,3,5-四-O-乙酰-L-核糖呋喃糖的β/α-异构体混合物转化为甲基-1-(2,3,5-三-O-乙酰-β-L-核糖呋喃糖基)-1,2,4-三唑-3-羧酸酯的方法，这是左环病毒素的中间体，以及新颖的纯α-异构体，α-1,2,3,5-四-O-乙酰-L-核糖呋喃糖，对于制造左环病毒素很有用。
• Reaction Kinetics and Mechanism of Sulfuric Acid-Catalyzed Acetolysis of Acylated Methyl L-Ribofuranosides
  作者：Jonas J. Forsman、Johan Wärnå、Dmitry Yu. Murzin、Reko Leino

  DOI：10.1002/ejoc.200900889

  日期：2009.11

  The mechanism of the sulfuric acid-catalyzed acetolysis of methyl 2,3,5-tri-O-acetyl- and methyl 2,3,5-tri-O-benzoyl-L-ribofuranosides and the accompanying anomerization of both the starting material and the 1,2,3,5-tetra-O-acetyl- and 1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranoses formed was investigated. The progress of the reactions was followed by 1H NMR spectroscopy and the rate constants for

  硫酸催化甲基 2,3,5-三-O-乙酰基-和甲基 2,3,5-三-O-苯甲酰基-L-呋喃核糖苷的乙酰化机理以及伴随的起始原料和研究了形成的 1,2,3,5-四-O-乙酰基-和 1-O-乙酰基-2,3,5-三-O-苯甲酰基-L-呋喃核糖。反应的进程由 1 H NMR 光谱跟踪，反应的速率常数被确定为建议的动力学模型。阐明了 H+ 和 Ac+ 作为催化活性物质的作用，证明酰化甲基呋喃糖苷的异构化是通过质子化激活的，而相反，1-O-乙酰基呋喃核糖的异构化是通过乙酰阳离子激活的.
• METHOD FOR PRODUCING FURANOSE DERIVATIVE
  申请人：Katsurada Manabu

  公开号：US20100105890A1

  公开（公告）日：2010-04-29

  An object of the present invention is to provide a industrially appropriate method for producing the β-anomers of ribofuranose derivatives in a highly selective manner at a high yield. The present invention provides a method for producing ribofuranose derivatives wherein β-anomers is precipitated from among the generated furanose derivatives by controlling the amount of a reaction reagent used and/or using a poor solvent in the acetolysis reactions of 2,3,5-tri-O-acyl- 1 -O-alkyl-ribofuranose and 2,3-di-O-acyl- 1 -O-alkyl-5-deoxy-ribofuranose.

  本发明的目的是提供一种工业上适用的方法，以高选择性和高产率生产核黄素糖苷衍生物的β-异构体。本发明提供了一种生产核黄素糖苷衍生物的方法，其中通过控制反应试剂的用量和/或使用劣质溶剂，在2,3,5-三-O-酰基-1-O-烷基-核黄素糖苷和2,3-二-O-酰基-1-O-烷基-5-去氧-核黄素糖苷的乙酰化反应中沉淀β-异构体。
• EP2105445
  申请人：——

  公开号：——

  公开（公告）日：——