(5R)-5-<(triphenylmethoxy)methyl>-γ-butyrolactol | 637741-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (5R)-5-<(triphenylmethoxy)methyl>-γ-butyrolactol
• 英文别名: 2,3-dideoxy-5-O-trityl-L-glyceropentanoic acid γ-lactol；(5R)-5-[(triphenylmethoxy)methyl]-γ-butyrolactol；(5R)-5-(trityloxymethyl)oxolan-2-ol
• CAS: 637741-83-4
• 化学式: C₂₄H₂₄O₃
• 分子量: 360.453
• InChiKey: QHBUYWDPCOLIBA-WTQRLHSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R)-5-<(triphenylmethoxy)methyl>-γ-butyrolactol 在 盐酸肼 、 sodium hydride 、 肼 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.0h， 生成 4-[(5R)-5-(trityloxymethyl)oxolan-2-yl]-1H-pyrazol-5-amine
  参考文献：
  名称：

  Syntheses of 2″,3″-Dideoxy-L-Glycero-PentofuranosylC-Nucleosides

  摘要：

  2',3'-Dideoxy-L-C-nucleosides, 4-amino-8-(2,3-dideoxy-L-glyceropentofuranosyl)pyrazolo[1,5-a]-1,3,5-triazines (9 and 10), 4-amino-7-(2,3-dideoxy-L-glyceropentofuranosyl)-3H,5H-pyrrolo[3,2-d]pyrimidines (17 and 18), 7-(2,3-dideoxy-L-glyceropentofuranosyl)-4-oxo-3H,5H-pyrrolo[3,2-d]pyrimidines (23 and 24) and 2,4-diamino-5-(2,3-dideoxy-L-glyceropentofuranosyl)pyrimidines (28 and 29) have been synthesized from L-gulonic gamma-lactone 1.

  DOI：

  10.1080/07328319608007389
• 作为产物：
  描述：

  (R)-γ-羟甲基-γ-丁内酯 (R)-4,5-二氢-5-羟甲基-2(3H)-呋喃酮 (R)-5-羟甲基-2-氧代四氢呋喃 在 二异丁基氢化铝 作用下， 以 吡啶 、 正己烷 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 (5R)-5-<(triphenylmethoxy)methyl>-γ-butyrolactol
  参考文献：
  名称：

  Syntheses of 2″,3″-Dideoxy-L-Glycero-PentofuranosylC-Nucleosides

  摘要：

  2',3'-Dideoxy-L-C-nucleosides, 4-amino-8-(2,3-dideoxy-L-glyceropentofuranosyl)pyrazolo[1,5-a]-1,3,5-triazines (9 and 10), 4-amino-7-(2,3-dideoxy-L-glyceropentofuranosyl)-3H,5H-pyrrolo[3,2-d]pyrimidines (17 and 18), 7-(2,3-dideoxy-L-glyceropentofuranosyl)-4-oxo-3H,5H-pyrrolo[3,2-d]pyrimidines (23 and 24) and 2,4-diamino-5-(2,3-dideoxy-L-glyceropentofuranosyl)pyrimidines (28 and 29) have been synthesized from L-gulonic gamma-lactone 1.

  DOI：

  10.1080/07328319608007389

文献信息

• Efficient Synthesis of trans- or cis-4(5)-(5-Aminomethyltetrahydrofuran-2-yl)imidazoles via Diazafulvene Intermediates: Synthetic Approach toward Human Histamine H4-Ligands
  作者：Shinya Harusawa、Lisa Araki、Hirotaka Terashima、Makoto Kawamura、Seiichiro Takashima、Yasuhiko Sakamoto、Takeshi Hashimoto、Yumiko Yamamoto、Atsushi Yamatodani、Takushi Kurihara

  DOI：10.1248/cpb.51.832

  日期：——

  unsubstituted imidazole moiety in good yields. This methodology also afforded an alternative synthetic route to trans- and cis-ethyl 4(5)-(5-hydroxymethyltetrahydrofuran-2-yl)imidazole carboxylates (5 and 6), reported previously. Also, 4(5)-[(2R,5S)-5-aminomethyltetrahydrofuran-2-yl]imidazole (+)-2 was synthesized from ethyl 4(5)-(2-deoxy-beta-D-ribofuranosyl)imidazole-1-carboxylate (35) via the four steps involving

  预期（+）-4（5）-[（2R，5R）-5-氨基甲基四氢呋喃-2-基]咪唑[（+）-1，imifuramine]及其2R，5S-立体异构体（+）-2为碱化合物以开发选择性的人类组胺H4受体配体。（+）-1的改进合成是通过将Bu3P / N，N，N'，N'-四甲基偶氮二甲酰胺（TMAD）处理带有未取代咪唑部分的二醇17ab生成的二氮烯富烯中间体进行环化来完成的。这种方法还提供了另一种合成途径，可以合成先前报道的4（5）-（5-羟甲基四氢呋喃-2-基）咪唑羧酸酯的反式和顺式（5和6）。另外，由乙基4（5）-（2-脱氧-β-D-核呋喃呋喃糖基）咪唑-乙基合成了4（5）-[（（2R，5S）-5-氨基甲基四氢呋喃-2-基]咪唑（+）-2。通过涉及脱氧的四个步骤使1-羧酸盐（35）。
• Enantio- and diastereoisomers of 2,4-dimethoxy-5-(2,3-dideoxy-5-O-tritylribofuranosyl)pyrimidine. 2',3'-Dideoxy pyrimidine C-nucleosides by palladium-mediated glycal-aglycon coupling
  作者：Han Cheng Zhang、G. Doyle Daves

  DOI：10.1021/jo00061a034

  日期：1993.4

  Newly available enantiomeric 2,3-dideoxy glycals, (5S)- and (5R)-4,5-dihydro-5-[(triphenylmethoxy)-methyl] furans and 2,4-dimethoxy-5-iodopyrimidine undergo palladium-mediated coupling by two different, complementary procedures to form enantiomeric pairs of (2',3'-dideoxy-2',3'-didehydrofuranosyl)- and (2',3'-dideoxy-3',4'-didehydrofuranosyl)pyrimidine C-nucleosides. Stereoselective reductions of the carbohydrate unsaturations produce all four enantio- and diastereoisomers of 2,4-dimethoxy-5-(2,3-dideoxy-5-O-tritylribofuranosyl)pyrimidine. The facile two-step syntheses of 2',3'-deoxy C-nucleosides which involves preparation of a D-series C-nucleoside from an L-series glycal (and vice versa) represents a new strategy for C-nucleoside synthesis.