甲基2-脱氧-2-亚甲基-beta-D-赤式-呋喃戊糖苷 | 229469-30-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基2-脱氧-2-亚甲基-beta-D-赤式-呋喃戊糖苷
• 中文别名: 4,5-二氢-N-甲基-1-[3-(三氟甲基)苯基]-1H-吡唑-3-胺
• 英文名称: (2R,3S,5S)-2-(hydroxymethyl)-5-methoxy-4-methylideneoxolan-3-ol
• CAS: 229469-30-1
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: MFCHNQFZFZNKTJ-VQVTYTSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基2-脱氧-2-亚甲基-beta-D-赤式-呋喃戊糖苷 在 吡啶 、 sodium perborate 、 9-borabicyclo[3.3.1]nonane dimer 、 四丁基氟化铵 、 sodium hydride 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 二甲基亚砜 为溶剂， 反应 31.5h， 生成 (2S,3S,4R,5S)-4-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-methoxy-3-phenylmethoxyoxolane-2-carbaldehyde
  参考文献：
  名称：

  Conformationally locked nucleosides. Synthesis and stereochemical assignments of 2′-C,4′-C-bridged bicyclonucleosides

  摘要：

  1-alpha-O-Methyl-3-O,5-O-TIPDS-arabinose was converted, in multiple steps, to 2,6-dioxabicyclo[3,2,1]octane derivatives, which were condensed with silylated nucleoside bases to give the desired 2',4'-bridged bicyclonucleosides. In this article, synthesis and stereochemical assignments of the bicyclonucleosides are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00394-4
• 作为产物：
  描述：

  methyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranoside 在 吡啶 、 四丁基氟化铵 、 草酸 、 sodium tert-pentoxide 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 14.0h， 生成 甲基2-脱氧-2-亚甲基-beta-D-赤式-呋喃戊糖苷
  参考文献：
  名称：

  Conformationally locked nucleosides. Synthesis and stereochemical assignments of 2′-C,4′-C-bridged bicyclonucleosides

  摘要：

  1-alpha-O-Methyl-3-O,5-O-TIPDS-arabinose was converted, in multiple steps, to 2,6-dioxabicyclo[3,2,1]octane derivatives, which were condensed with silylated nucleoside bases to give the desired 2',4'-bridged bicyclonucleosides. In this article, synthesis and stereochemical assignments of the bicyclonucleosides are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00394-4

文献信息

• Conformationally Locked Nucleoside Analogs. Synthesis of 2′-Deoxy-2′-C, 4′-C-Bridged Bicyclic Nucleosides
  作者：Guangyi Wang、Esmir Gunic

  DOI：10.1080/15257779908041488

  日期：1999.4

  1-alpha-Methylarabinose was converted, in three steps, to 2-deoxy-2-methyleneribose derivative 3, which was subjected to hydroboration to give 2-alpha-hydroxymethyl derivative 4 exclusively; 4 was converted to 2,4-bis(hydroxymethyl)ribose derivative 6 in four steps. Mesylation, detritylation, and ring closure, followed by hydrolysis of the mesyl group at O5, gave 3,6-dioxabicyclo[3,2,1]octane derivative 8. After acetylation, 8 was coupled with silylated 6-chloropurine to give desired alpha- and beta-bicyclic-sugar nucleosides.
• NOVEL NUCLEOSIDES HAVING BICYCLIC SUGAR MOIETY
  申请人：ICN Pharmaceuticals, Inc.

  公开号：EP1082012A1

  公开（公告）日：2001-03-14
• EP1082012A4
  申请人：——

  公开号：EP1082012A4

  公开（公告）日：2002-01-16
• [EN] NOVEL NUCLEOSIDES HAVING BICYCLIC SUGAR MOIETY<br/>[FR] NOUVEAUX NUCLEOSIDES COMPORTANT UNE FRACTION SUCRE BICYCLIQUE
  申请人：ICN PHARMACEUTICALS, INC.

  公开号：WO1999060855A1

  公开（公告）日：1999-12-02

  (EN) Conformationally restricted 2',4'-bridged nucleoside analogues are described herein. The compounds can be prepared by cyclization at C2' and C4' of nucleosides through a linker or linking molecule. These novel nucleosides have a desired, locked sugar pucker and are potentially useful as pharmaceutical ingredients. Oligonucleotides composed of these novel nucleosides are useful for oligonucleotide therapeutic and diagnostic compounds.(FR) On décrit des analogues de nucléosides 2',4'-pontés à conformation limitée. Ces composés peuvent être préparés par cyclisation en C2' et C4' des nucléosides au moyen d'un lieur ou d'une molécule de liaison. Ces nouveaux nucléosides présentent un fronçage sucre fermé et peuvent être utiles comme ingrédients pharmaceutiques. Les oligonucléotides constitués desdits nouveaux nucléosides peuvent entrer dans des composés oligonucléotidiques destinés à un usage diagnostique ou thérapeutique.
• Conformationally locked nucleosides. Synthesis and stereochemical assignments of 2′-C,4′-C-bridged bicyclonucleosides
  作者：Guangyi Wang、Jean-Luc Girardet、Esmir Gunic

  DOI：10.1016/s0040-4020(99)00394-4

  日期：1999.6

  1-alpha-O-Methyl-3-O,5-O-TIPDS-arabinose was converted, in multiple steps, to 2,6-dioxabicyclo[3,2,1]octane derivatives, which were condensed with silylated nucleoside bases to give the desired 2',4'-bridged bicyclonucleosides. In this article, synthesis and stereochemical assignments of the bicyclonucleosides are described. (C) 1999 Elsevier Science Ltd. All rights reserved.