(1R,6R,8R)-6-benzyloxy-1-(4,4'-dimethoxytrityloxymethyl)-8-(thymin-1-yl)-3,9-dioxabicyclo[4.3.0]nonane | 1112393-31-3

• 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: (1R,6R,8R)-6-benzyloxy-1-(4,4'-dimethoxytrityloxymethyl)-8-(thymin-1-yl)-3,9-dioxabicyclo[4.3.0]nonane
• 英文别名: 1-[(2R,3aR,7aR)-7a-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3a-phenylmethoxy-3,4,5,7-tetrahydro-2H-furo[2,3-c]pyran-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1112393-31-3
• 化学式: C₄₁H₄₂N₂O₈
• 分子量: 690.793
• InChiKey: UDCUZIDWPZSVML-UQLTYJDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  51
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R,6R,8R)-6-benzyloxy-1-(4,4'-dimethoxytrityloxymethyl)-8-(thymin-1-yl)-3,9-dioxabicyclo[4.3.0]nonane 在 palladium(II) hydroxide/carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以86%的产率得到(1S,6R,8R)-6-hydroxy-1-hydroxymethyl-8-(thymin-1-yl)-3,9-dioxabicyclo[4.3.0]nonane
  参考文献：
  名称：

  Synthesis of Bicyclic 2′-Deoxynucleosides with α-l-ribo- and β-d-xylo-Configurations and Restricted S- and N-Type Conformations

  摘要：

  Two bicyclic 2'-deoxynucleoside analogues are synthesized in 12 steps each from thymidine. With a six-membered ring fused to the C3'-C4' bond and an alpha-L-ribo- and a beta-D-xylo-configuration, these are con formationally restricted in an S- and an N-type conformation, respectively. The constitutions were proven by X-ray crystallography. ne beta-D-xylo-configured analogue is successfully converted to a 3'-phosphoramidite and incorporated into oligodeoxynucleotides, which are found to hybridize to DNA and RNA complements with decreased affinity.

  DOI：

  10.1021/jo8023472
• 作为产物：
  描述：

  1N-[3'-O-benzyl-5'-O-(4,4-dimethoxytrityl)-3'-C-(2-hydroxyethyl)-4'-C-methanesulfonyloxymethyl-2'-deoxy-β-D-xylofuranosyl]thymine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 oil 为溶剂， 以68%的产率得到(1R,6R,8R)-6-benzyloxy-1-(4,4'-dimethoxytrityloxymethyl)-8-(thymin-1-yl)-3,9-dioxabicyclo[4.3.0]nonane
  参考文献：
  名称：

  Synthesis of Bicyclic 2′-Deoxynucleosides with α-l-ribo- and β-d-xylo-Configurations and Restricted S- and N-Type Conformations

  摘要：

  Two bicyclic 2'-deoxynucleoside analogues are synthesized in 12 steps each from thymidine. With a six-membered ring fused to the C3'-C4' bond and an alpha-L-ribo- and a beta-D-xylo-configuration, these are con formationally restricted in an S- and an N-type conformation, respectively. The constitutions were proven by X-ray crystallography. ne beta-D-xylo-configured analogue is successfully converted to a 3'-phosphoramidite and incorporated into oligodeoxynucleotides, which are found to hybridize to DNA and RNA complements with decreased affinity.

  DOI：

  10.1021/jo8023472

文献信息

• Synthesis of Bicyclic 2′-Deoxynucleosides with α-<scp>l</scp>-<i>ribo</i>- and β-<scp>d</scp>-<i>xylo</i>-Configurations and Restricted <i>S</i>- and <i>N</i>-Type Conformations
  作者：Khalil I. Shaikh、Surender Kumar、Lene Lundhus、Andrew D. Bond、Pawan K. Sharma、Poul Nielsen

  DOI：10.1021/jo8023472

  日期：2009.2.20

  Two bicyclic 2'-deoxynucleoside analogues are synthesized in 12 steps each from thymidine. With a six-membered ring fused to the C3'-C4' bond and an alpha-L-ribo- and a beta-D-xylo-configuration, these are con formationally restricted in an S- and an N-type conformation, respectively. The constitutions were proven by X-ray crystallography. ne beta-D-xylo-configured analogue is successfully converted to a 3'-phosphoramidite and incorporated into oligodeoxynucleotides, which are found to hybridize to DNA and RNA complements with decreased affinity.