1′-O-benzyl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranoside | 135246-59-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1′-O-benzyl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranoside
• 英文别名: 2',3',5'-tri-O-acetyl-1'-O-benzyl-β-D-ribofuranoside；1-O-benzyl-β-D-ribofuranose-2,3,5-triacetate；1-O-benzyl-beta-D-ribofuranose-2,3,5-triacetate；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-phenylmethoxyoxolan-2-yl]methyl acetate
• CAS: 135246-59-2
• 化学式: C₁₈H₂₂O₈
• 分子量: 366.368
• InChiKey: KLDPDRCSPYFUSF-BRSBDYLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1′-O-benzyl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranoside 在 氢气 、 氯化铵 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.5h， 生成 4,5-dimethyl-2-nitro-N-(2',3',5'-tri-O-acetyl-α-D-ribofuranosyl)benzenamine
  参考文献：
  名称：

  Synthesis and Properties of Flavin Ribofuranosides and Flavin Ribopyranosides

  摘要：

  Ribose-containing coenzymes like flavin mononucleotide (FMN) can be considered to be fossils of a prebiotic RNA world in which RNA encoded genetic information and catalyzed chemical reactions. To investigate the catalytic and base-pairing properties of FMN-containing oligonucleotides, the two cyclic flavin beta-D-ribosides 3 and 4 derived from riboflavin 2 were synthesized (Schemes 1 and 2). These are both constitutionally strongly related to the nucleobase uridine and should be able to participate as catalytically competent and informational nucleobases in DNA RNA, and p-RNA. Ribofuranaside 3 was too unstable to be isolated, but ribopyranoside 4 had the required stability, beta-D-configuration, and anti-conformation of the glycosidic bond.

  DOI：

  10.1002/1522-2675(20000906)83:9<2452::aid-hlca2452>3.0.co;2-6
• 作为产物：
  描述：

  D-核糖 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 以 吡啶 、 水 为溶剂， 生成 1′-O-benzyl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis and Properties of Flavin Ribofuranosides and Flavin Ribopyranosides

  摘要：

  Ribose-containing coenzymes like flavin mononucleotide (FMN) can be considered to be fossils of a prebiotic RNA world in which RNA encoded genetic information and catalyzed chemical reactions. To investigate the catalytic and base-pairing properties of FMN-containing oligonucleotides, the two cyclic flavin beta-D-ribosides 3 and 4 derived from riboflavin 2 were synthesized (Schemes 1 and 2). These are both constitutionally strongly related to the nucleobase uridine and should be able to participate as catalytically competent and informational nucleobases in DNA RNA, and p-RNA. Ribofuranaside 3 was too unstable to be isolated, but ribopyranoside 4 had the required stability, beta-D-configuration, and anti-conformation of the glycosidic bond.

  DOI：

  10.1002/1522-2675(20000906)83:9<2452::aid-hlca2452>3.0.co;2-6
• 作为试剂：
  描述：

  苯甲醇 、 四乙酰核糖 、 碳酸氢钠 、 sodium methylate 、 甲醇 在 溴化锌 甲苯 、 氯化钠 、 magnesium sulfate 、 1′-O-benzyl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranoside 、 甲醇 、 silica gel 作用下， 以 甲苯 为溶剂， 反应 22.0h， 生成 benzyl-β-D-ribofuranoside
  参考文献：
  名称：

  Method for producing beta-D-ribofuranose derivatives or optical isomers thereof

  摘要：

  本发明提供了一种高效生产&bgr;-D-核糖呋喃衍生物或其光学异构体的方法，该方法可用作制药核酸系列产品的合成中间体。该方法包括以下步骤：在酸催化剂的存在下，通过使&bgr;-D-核糖呋喃-1,2,3,5-四乙酸酯或其光学异构体与苄醇反应，生产1-O-苄基-&bgr;-D-核糖呋喃-2,3,5-三乙酸酯或其光学异构体；在碱的存在下，水解所得的1-O-苄基-&bgr;-D-核糖呋喃-2,3,5-三乙酸酯，生产1-O-苄基-&bgr;-D-核糖呋喃或其光学异构体。

  公开号：

  US20020187942A1

文献信息

• Synthesis of a 3′-Fluoro-3′-deoxytetrose Adenine Phosphonate
  作者：Swarup De、Steven De Jonghe、Piet Herdewijn

  DOI：10.1021/acs.joc.7b01482

  日期：2017.9.15

  adenine phosphonate has been developed. The synthesis starts from l-xylose and key steps include the stereospecific introduction of the phosphonomethoxy group and adenine. In addition, a regioselective fluorination reaction allows access to the desired 3′-fluoro-3′-deoxytetrose moiety. This methodology allows the straightforward synthesis of a 3′-fluoro-3′-deoxytetrose adenine phosphonate and can be

  已开发出一种新的合成途径来合成3'-氟-3'-脱氧etroseetrose腺嘌呤膦酸酯。合成从1-木糖开始，关键步骤包括膦酰基甲氧基和腺嘌呤的立体定向引入。另外，区域选择性氟化反应允许进入所需的3'-氟-3'-脱氧四糖部分。该方法允许直接合成3'-氟-3'-脱氧山梨糖腺嘌呤膦酸酯，并且可以扩展为合成其他类型的3'-氟核苷膦酸酯。
• Method for producing a beta-D-ribofuranose derivative or an optical isomer thereof
  申请人：Ajinomoto Co., Inc.

  公开号：EP1260516A1

  公开（公告）日：2002-11-27

  The invention provides a method for efficiently producing β-D-ribofuranose derivatives or optical isomers thereof, useful as synthetic intermediates of pharmaceutical nucleic acid-series products. The method comprises a step of producing 1-O-benzyl-β-D-ribofuranose-2,3,5-triacetate or an optical isomer thereof by allowing β-D-ribofuranose-1,2,3,5-tetraacetate or an optical isomer thereof to react with benzyl alcohols in the presence of acid catalysts and a step of hydrolyzing the resulting 1-O-benzyl-β-D-ribofuranose-2,3,5-triacetate in the presence of a base to produce 1-O-benzyl-β-D-ribofuranose or an optical isomer thereof.

  本发明提供了一种高效生产β-D-核糖呋喃衍生物或其光学异构体的方法，该方法可用作制备药物核酸系列产品的合成中间体。该方法包括以下步骤：在酸催化剂的存在下，使β-D-核糖呋喃-1,2,3,5-四乙酸酯或其光学异构体与苄醇反应，以生产1-O-苄基-β-D-核糖呋喃-2,3,5-三乙酸酯或其光学异构体；在碱的存在下水解所得的1-O-苄基-β-D-核糖呋喃-2,3,5-三乙酸酯，以生产1-O-苄基-β-D-核糖呋喃或其光学异构体。
• Method for producing &bgr;-D-ribofuranose derivatives or optical isomers thereof
  申请人：Ajinomoto Co., Inc.

  公开号：US06800742B2

  公开（公告）日：2004-10-05

  The present invention provides a method for efficiently producing &bgr;-D-ribofuranose derivatives or optical isomers thereof, useful as synthetic intermediates of pharmaceutical nucleic acid-series products. The method comprises a step of producing 1-O-benzyl-&bgr;-D-ribofuranose-2,3,5-triacetate or an optical isomer thereof by allowing &bgr;-D-ribofuranose-1,2,3,5-tetraacetate or an optical isomer thereof to react with a benzyl alcohol in the presence of acid catalysts and a step of hydrolyzing the resulting 1-O-benzyl-&bgr;-D-ribofuranose-2,3,5-triacetate in the presence of a base to produce 1-O-benzyl-&bgr;-D-ribofuranose or an optical isomer thereof.

  本发明提供了一种有效生产&bgr;-D-核糖呋喃衍生物或其光学异构体的方法，该方法可用作制药核酸类产品的合成中间体。该方法包括以下步骤：在酸催化剂的存在下，使&bgr;-D-核糖呋喃-1,2,3,5-四乙酸酯或其光学异构体与苄醇反应，生成1-O-苄基-&bgr;-D-核糖呋喃-2,3,5-三乙酸酯或其光学异构体；在碱的存在下，水解所得的1-O-苄基-&bgr;-D-核糖呋喃-2,3,5-三乙酸酯，生成1-O-苄基-&bgr;-D-核糖呋喃或其光学异构体。
• β−Ｄ−リボフラノース誘導体又はその光学異性体の製造方法
  申请人：——

  公开号：JP2002338593A

  公开（公告）日：2002-11-27

  (57)【要約】 （修正有）\n【課題】 核酸系医薬品の合成中間体として有用なβ−Ｄ−リボフラノース誘導体又はその光学異性体を効率的な製造方法の提供。\n【解決手段】 下記式の合成工程に従ってβ−Ｄ−リボフラノース−１，２，３，５−テトラアセテート又はその光学異性体を酸触媒下、ベンジルアルコール類と反応させて１−Ｏ−ベンジル−β−Ｄ−リボフラノース−２，３，５−トリアセテート又はその光学異性体を製造する。得られた１−Ｏ−ベンジル−β−Ｄ−リボフラノース−２，３，５−トリアセテートを塩基の存在下に加水分解して１−Ｏ−ベンジル−β−Ｄ−リボフラノース又はその光学異性体を製造する。\n

  (57) [摘要]（有修改） Јn[主题] 提供一种生产β-D-呋喃核糖衍生物或其光学异构体的有效方法，该衍生物或其光学异构体可用作核酸类药物的合成中间体。\按照下式的合成工艺，β-D-呋喃核糖-1,2,3,5-四乙酸酯或其光学异构体在酸催化下与苄醇反应，得到 11-O-苄基-β-D-呋喃核糖-2,3,5-三乙酸酯或其光学异构体在酸催化下按下式合成工艺与苄醇反应得到 1-O-苄基-β-D-呋喃核糖-2,3,5-三乙酸酯或其光学异构体。反应按以下步骤进行。生成的 1-O-苄基-β-D-呋喃核糖-2,3,5-三乙酸酯在碱存在下水解水解生成 1-O-苄基-β-D-呋喃核糖或其光学异构体。\n
• Highly Efficient <i>O</i>-Glycosylations with <i>p</i>-Tolyl Thioribosides and <i>p</i>-TolSOTf
  作者：Michio Kurosu、Kai Li

  DOI：10.1021/jo801408x

  日期：2008.12.19

  GraphicsA wide variety of p-tolyl thioriboside donors are examined for O-ribosylations of primary and secondary alcohols. p-Tolylsulfenyl trifluoromethanesulfonate (p-TolSOTf) is very effective in promoting O-ribosylations with p-tolyl thioriboside; all reactions are completed within 1-15 min to provide the desired products in good yield with reliable alpha/beta selectivity. A wide range of functional groups are tolerated under these conditions. The described O-ribosylation conditions are very useful for the generation of ribosaminouridine library molecules in solution or on polymer support.