3-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribofuranose
• 英文别名: 3-deoxy-1,2-O-isopropylidene-3-C-methyl-D-ribo-furanose；((3aR,5S,6R,6aR)-2,2,6-trimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol；3-Desoxy-O¹,O²-isopropyliden-3-methyl-α-D-ribofuranose；((3aR,5S,6R,6aR)-2,2,6-trimethyltetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methanol；[(3aR,5S,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: QSFFQPSPYRVHMA-WCTZXXKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribofuranose 在 溴 、 sodium hydride 、 potassium carbonate 、 barium benzoate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2S,3R,4S)-3-methyl-4-(phenylmethoxymethyl)oxetane-2-carboxylate
  参考文献：
  名称：

  Ring contraction of 3-deoxy-2-O-trifluoromethanesulphonates of α-hydroxy-γ-lactones to oxetanes

  摘要：

  DOI：

  10.1016/s0040-4039(00)97209-5
• 作为产物：
  描述：

  3-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-allofuranose 在 sodium tetrahydroborate 、 sodium periodate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 3-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribofuranose
  参考文献：
  名称：

  A carbohydrate approach for the formal total synthesis of the prostacyclin analogue (16S)-iloprost

  摘要：

  The formal total synthesis of the synthetic and stable analogue of prostacyclin, (16S)- iloprost is described via a convergent synthesis starting from readily available D-glucose. Julia olefination and the aldol reaction are the key steps involved in the synthesis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.005

文献信息

• Total syntheses of Prelactone V and Prelactone B
  作者：S. Raghavendra、Krishnaji Tadiparthi、J.S. Yadav

  DOI：10.1016/j.carres.2017.02.008

  日期：2017.4

  products Prelactone-V and Prelactone-B have been accomplished by a novel Chiron approach starting from d-glucose. The synthesis involves isopropylidene acetal formation of d-glucose using Poly(4-vinylpyridine) supported iodine as a catalyst, Tebbe olefination, Grignard reaction, Wittig olefination, selective mono deprotection of acetal using PMA/SiO2, hydrogenation and anti-1,3-diol formation are as

  天然产物Prelactone-V和Prelactone-B的总合成已通过从D-葡萄糖href=https://www.molaid.com/MS_9248 target="_blank">葡萄糖开始的新型Chiron方法完成。合成涉及使用聚（4-乙烯基吡啶）负载的碘作为催化剂的D-葡萄糖的异亚丙基缩醛形成，Tebbe烯烃化，Grignard反应，Wittig烯烃化，使用PMA / SiO2进行的乙醛选择性单脱保护，氢化和抗1,3-3二醇的形成是关键步骤。
• LIPID FORMULATED SINGLE STRANDED RNA
  申请人：Manoharan Muthiah

  公开号：US20130156845A1

  公开（公告）日：2013-06-20

  The present invention provides compositions comprising a nucleic acid lipid particle and an oligomeric compound and uses thereof. In certain embodiments, such compositions are useful as antisense compounds. Certain such antisense compounds are useful as RNase H antisense compounds or as RNAi compounds.

  本发明提供了包含核酸脂质粒子和寡核苷酸化合物的组合物及其用途。在某些实施方式中，这些组合物可用作反义物质。某些这样的反义物质可用作RNase H反义物质或RNAi物质。
• Carbohydrate-based approach to four enantiomerically pure 2-naphthylmethyl 3-hydroxy-2-methylbutanoates
  作者：Bogdan Doboszewski、Piet Herdewijn

  DOI：10.1016/j.tetlet.2007.12.104

  日期：2008.2

  Chiral pool approach using d-glucose, l-xylose, and d- and l-arabinoses was used to obtain four stereoisomeric 3-hydroxy-2-methylbutanoic acids with well defined configurations. The acids were isolated as fluorescent 2-naphthylmethyl esters after reaction with 2-naphthyldiazomethane.

  使用d-葡萄糖，l-木糖以及d-和l-阿拉伯糖的手性库法获得了具有明确定义构型的四种立体异构体3-羟基-2-甲基丁酸。与2-萘基重氮甲烷反应后，分离出作为荧光的2-萘基甲基酯的酸。
• Botrylactone Synthesis and Structure Revision: A Convergent Approach from D-Glucose
  作者：Wilfried Bruns、Stefan Horns、Hartmut Redlich

  DOI：10.1055/s-1995-3904

  日期：1995.3

  A convergent approach for the synthesis of botrylactone 1, an antibiotic from the fungus Botrytis cinerea, from D-glucose is presented. The synthesis is carried out with an overall yield of 0.74% and a diastereoselectivity of >95%. The originally published structure 2 must be revised.

  提出了一种从 D-葡萄糖合成葡萄内酯 1（一种来自灰葡萄孢真菌的抗生素）的聚合方法。合成的总产率为0.74%，非对映选择性>95%。必须修改最初发布的结构2。
• OLIGOMERIC COMPOUNDS AND METHODS
  申请人：Swayze Eric E.

  公开号：US20110313019A1

  公开（公告）日：2011-12-22

  The present invention provides oligomeric compounds and uses thereof. In certain embodiments, such oligomeric compounds are useful as antisense compounds. Certain such antisense compounds are useful as RNase H antisense compounds or as RNAi compounds.

  本发明提供了寡聚物化合物及其用途。在某些实施例中，这些寡聚物化合物可用作反义物质。某些这样的反义物质可用作RNase H反义物质或RNAi化合物。