1-[(6aR,8R,9R,9aR)-9-bromo-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]pyrimidine-2,4-dione | 148504-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(6aR,8R,9R,9aR)-9-bromo-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]pyrimidine-2,4-dione
• CAS: 148504-66-9
• 化学式: C₂₁H₃₇BrN₂O₆Si₂
• 分子量: 549.61
• InChiKey: JGDQYVLAGFWEHL-VBSBHUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(6aR,8R,9R,9aR)-9-bromo-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]pyrimidine-2,4-dione 在 (Me₃Si)3Si⁽²⁾H-Et₃B 作用下， 以 四氢呋喃 为溶剂， 以10%的产率得到3',5'-O-(1,1,3,3-四异丙基-1,3-DISILOXANEDIYL)-2'-脱氧尿苷
  参考文献：
  名称：

  Tris(trimethylsilyl)[2H]silane-triethylborane system producing the highly diastereoselective deuteration (> 99:1) of 2′-bromo-2′-deoxy- and 2′-O-phenoxythiocarbonylribonucleosides at 0°C

  摘要：

  Reductive protylation and deuteration reactions using (Me3Si)(3)SiH- and (Me3Si)(3)(SiH)-H-2-Et3B systems were investigated in view of the differences in bond energy and bond length between the Si-H of (Me3Si)(3)SiH and the Sn-H of Bu3SnH. Higher diastereoselectivity was obtained in comparison with the reactions using the Bu3SnH - and (Bu3SnH)-H-2-Et3B systems; the (Me3Si)(3)SiH system gave remarkable diastereoselectivity of 98.7% at 0 degrees C, whereas the other system required temperatures below -70 degrees C. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01722-x
• 作为产物：
  描述：

  2,2'-脱水尿苷 在 三氟化硼乙醚 、 lithium bromide 作用下， 以 1,4-二氧六环 、 吡啶 为溶剂， 反应 30.0h， 生成 1-[(6aR,8R,9R,9aR)-9-bromo-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  Efficient Synthesis of 2′-Bromo-2′-Deoxy-3′,5′-O-TPDS-pyrimidine Nucleosides by Boron Trifluoride Catalyzed Reaction of O²,2′-Anhydro-(1-β-D-Arabinofuran0Syl)pyrimidine Nucleosides with Lithium Bromide

  摘要：

  Efficient syntheses of 2'-bromo-2'-deoxy-3',5'-O-TPDS-uridine (5a) and 1-(2-bromo-3,5-O-TPDS-beta-D-ribofuranosyl)thymine (5b) from uridine and 1-(beta-D-ribofuranosyl)thymine are described, respectively. The key step is a treatment of 3',5'-O-TPDS-O-2,2'-anhydro-1-(beta-D-arabinofuranosyl)uracil (4a) and -thymine (4b) with LiBr in the presence of BF3-OEt(2) in 1,4-dioxane at 60 degrees C to give 5a and 5b in 98%, and 96% yield, respectively.

  DOI：

  10.1080/07328319608002418

文献信息

• Efficient Synthesis of 2′-Bromo-2′-Deoxy-3′,5′-<i>O</i>-TPDS-pyrimidine Nucleosides by Boron Trifluoride Catalyzed Reaction of O²,2′-Anhydro-(1-β-D-Arabinofuran0Syl)pyrimidine Nucleosides with Lithium Bromide
  作者：Yukio Aoyama、Takeshi Sekine、Yoshiaki Iwamoto、Etsuko Kawashima、Yoshiharu Ishido

  DOI：10.1080/07328319608002418

  日期：1996.1

  Efficient syntheses of 2'-bromo-2'-deoxy-3',5'-O-TPDS-uridine (5a) and 1-(2-bromo-3,5-O-TPDS-beta-D-ribofuranosyl)thymine (5b) from uridine and 1-(beta-D-ribofuranosyl)thymine are described, respectively. The key step is a treatment of 3',5'-O-TPDS-O-2,2'-anhydro-1-(beta-D-arabinofuranosyl)uracil (4a) and -thymine (4b) with LiBr in the presence of BF3-OEt(2) in 1,4-dioxane at 60 degrees C to give 5a and 5b in 98%, and 96% yield, respectively.
• Tris(trimethylsilyl)[2H]silane-triethylborane system producing the highly diastereoselective deuteration (&gt; 99:1) of 2′-bromo-2′-deoxy- and 2′-O-phenoxythiocarbonylribonucleosides at 0°C
  作者：Etsuko Kawashima、Seishiro Uchida、Masayoshi Miyahara、Yoshiharu Ishido

  DOI：10.1016/s0040-4039(97)01722-x

  日期：1997.10

  Reductive protylation and deuteration reactions using (Me3Si)(3)SiH- and (Me3Si)(3)(SiH)-H-2-Et3B systems were investigated in view of the differences in bond energy and bond length between the Si-H of (Me3Si)(3)SiH and the Sn-H of Bu3SnH. Higher diastereoselectivity was obtained in comparison with the reactions using the Bu3SnH - and (Bu3SnH)-H-2-Et3B systems; the (Me3Si)(3)SiH system gave remarkable diastereoselectivity of 98.7% at 0 degrees C, whereas the other system required temperatures below -70 degrees C. (C) 1997 Elsevier Science Ltd.