1β-{3-[(pyrrolidin-1-yl)carbonyl]phenyl}-1-deoxy-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose | 1166384-98-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1β-{3-[(pyrrolidin-1-yl)carbonyl]phenyl}-1-deoxy-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose
• 英文别名: [3-[(2S,3S,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]phenyl]-pyrrolidin-1-ylmethanone
• CAS: 1166384-98-0
• 化学式: C₃₄H₆₃NO₅Si₃
• 分子量: 650.134
• InChiKey: VKDGYYURRSWNFV-ATIZSFMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.17
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1β-{3-[(pyrrolidin-1-yl)carbonyl]phenyl}-1-deoxy-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose 在 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以86%的产率得到1β-{3-[(pyrrolidin-1-yl)carbonyl]phenyl}-1-deoxy-D-ribofuranose
  参考文献：
  名称：

  Synthesis of benzamide-C-ribonucleosides by Pd-catalyzed aminocarbonylations

  摘要：

  A novel modular, efficient and practical methodology for preparation of p- and m-substituted benzamide-C-ribonucleosides was developed. Reaction of TBS-protected 3- and 4-bromophenyl-C-ribonucleosides 1 and 4 with Various primary and secondary amines or NH4Cl Under atmospheric pressure Of carbon monoxide and in the Presence of Pd(OAc)(2) and Xantphos lead to the corresponding amides 2a-j and 5a-j in high yields. Subsequent deprotection of silylated nucleosides by Et3N center dot 3HF or TFA afforded a series of free C-ribonucleosides 3a-j or 6a-j in excellent yields (20 examples). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.006
• 作为产物：
  描述：

  四氢吡咯 、 1β-(3-bromophenyl)-1-deoxy-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose 、 一氧化碳 在 potassium phosphate 、 palladium diacetate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 以95%的产率得到1β-{3-[(pyrrolidin-1-yl)carbonyl]phenyl}-1-deoxy-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose
  参考文献：
  名称：

  Synthesis of benzamide-C-ribonucleosides by Pd-catalyzed aminocarbonylations

  摘要：

  A novel modular, efficient and practical methodology for preparation of p- and m-substituted benzamide-C-ribonucleosides was developed. Reaction of TBS-protected 3- and 4-bromophenyl-C-ribonucleosides 1 and 4 with Various primary and secondary amines or NH4Cl Under atmospheric pressure Of carbon monoxide and in the Presence of Pd(OAc)(2) and Xantphos lead to the corresponding amides 2a-j and 5a-j in high yields. Subsequent deprotection of silylated nucleosides by Et3N center dot 3HF or TFA afforded a series of free C-ribonucleosides 3a-j or 6a-j in excellent yields (20 examples). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.006

文献信息

• Synthesis of benzamide-C-ribonucleosides by Pd-catalyzed aminocarbonylations
  作者：Martin Štefko、Radek Pohl、Michal Hocek

  DOI：10.1016/j.tet.2009.04.006

  日期：2009.6

  A novel modular, efficient and practical methodology for preparation of p- and m-substituted benzamide-C-ribonucleosides was developed. Reaction of TBS-protected 3- and 4-bromophenyl-C-ribonucleosides 1 and 4 with Various primary and secondary amines or NH4Cl Under atmospheric pressure Of carbon monoxide and in the Presence of Pd(OAc)(2) and Xantphos lead to the corresponding amides 2a-j and 5a-j in high yields. Subsequent deprotection of silylated nucleosides by Et3N center dot 3HF or TFA afforded a series of free C-ribonucleosides 3a-j or 6a-j in excellent yields (20 examples). (C) 2009 Elsevier Ltd. All rights reserved.