tert-butyl N-[(1S,2R,4R,5R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-oxabicyclo[3.1.0]hexan-2-yl]carbamate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: tert-butyl N-[(1S,2R,4R,5R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-oxabicyclo[3.1.0]hexan-2-yl]carbamate
• 化学式: C₁₇H₃₃NO₄Si
• 分子量: 343.539
• InChiKey: SECGTRNNHCDUQG-SYQHCUMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  60.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S,2R,4R,5R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-oxabicyclo[3.1.0]hexan-2-yl]carbamate 在 水 、 红铝 作用下， 以 甲苯 为溶剂， 生成 (+)-(1S,2R,4R)-4-氨基-2-(羟甲基)-1-环戊醇
  参考文献：
  名称：

  2-Azabicyclo [2.2.1] hept-5-en-3-one epoxy：通用的中间体，用于合成环戊基碳环2-脱氧，3-脱氧和阿拉伯核糖核苷类似物

  摘要：

  5，6-环氧-外-2--2-氮杂双环[2.2.1]庚-3-已被用作合成2-脱氧，3-脱氧和芳基-环戊基碳环核苷的通用中间体。报道了（+）碳环胸苷13的有效的，短的合成。

  DOI：

  10.1016/s0040-4039(99)01113-2
• 作为产物：
  描述：

  tert-butyl (1S,2R,4S,5R)-7-oxo-3-oxa-6-azatricyclo[3.2.1.0^2,4]octan-6-carboxylate 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 tert-butyl N-[(1S,2R,4R,5R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-oxabicyclo[3.1.0]hexan-2-yl]carbamate
  参考文献：
  名称：

  2-Azabicyclo [2.2.1] hept-5-en-3-one epoxy：通用的中间体，用于合成环戊基碳环2-脱氧，3-脱氧和阿拉伯核糖核苷类似物

  摘要：

  5，6-环氧-外-2--2-氮杂双环[2.2.1]庚-3-已被用作合成2-脱氧，3-脱氧和芳基-环戊基碳环核苷的通用中间体。报道了（+）碳环胸苷13的有效的，短的合成。

  DOI：

  10.1016/s0040-4039(99)01113-2

文献信息

• 2-Azabicyclo[2.2.1]hept-5-en-3-one epoxide: A versatile intermediate for the synthesis of cyclopentyl carbocyclic 2-deoxy-, 3-deoxy- & ara- ribonucleoside analogues
  作者：Belén M Domínguez、Paul M Cullis

  DOI：10.1016/s0040-4039(99)01113-2

  日期：1999.7

  5,6-Epoxy-exo-2-azabicyclo[2.2.1]heptan-3-one has been used as a versatile intermediate in the synthesis of 2-deoxy-, 3-deoxy- and ara- cyclopentyl carbocyclic nucleosides. An efficient, short synthesis of the (+) carbocyclic thymidine 13 is reported.

  5，6-环氧-外-2--2-氮杂双环[2.2.1]庚-3-已被用作合成2-脱氧，3-脱氧和芳基-环戊基碳环核苷的通用中间体。报道了（+）碳环胸苷13的有效的，短的合成。
• Base Pairing and Replicative Processing of the Formamidopyrimidine-dG DNA Lesion
  作者：Matthias Ober、Heiko Müller、Carsten Pieck、Johannes Gierlich、Thomas Carell

  DOI：10.1021/ja0549188

  日期：2005.12.1

  The 2,6-diamino-4-hydroxy-5-formamidopyrimidine of 2'-deoxyguanosine (FaPydG) is one of the major DNA lesions found after oxidative stress in cells. To clarify the base pairing and coding potential of this major DNA lesion with the aim to estimate its mutagenic effect, we prepared oligonucleotides containing a cyclopentane based analogue of the DNA lesion (cFaPydG). In addition, oligonucleoticles containing the cyclopentane analogue of 2'-deoxyguanosine (cdG), and oligonucleotides containing 8-oxo-7,8-dihydro2'-deoxyguanosine (8-oxodG) were synthesized. The thermodynamic stability of duplexes containing these building blocks and all canonical counterbases were determined by concentration dependent melting-point measurements (van't Hoff plots). The data reveal that cFaPydG greatly destabilizes a DNA duplex (Delta Delta G(o)298K approximate to 2-4 kcal mol(-1)). The optimal base pairing partner for the cFaPydG lesion is dC. Investigation of duplexes containing dG and cdG shows that the effect of substituting the deoxyribose by a cyclopentane moiety is marginal. The data also provide strong evidence that the FaPydG lesion is unable to form a base pair with dA. Our computational studies indicate that the syn-conformation required for base pairing with dA is energetically unfavorable. This is in contrast to 8-oxodG for which the syn-conformation represents the energetic minimum. Kinetic primer extension studies using S. cerevisiae Pol eta reveal that cFaPydG is replicated in an error-free fashion. dC is inserted 2-3 orders of magnitude more efficiently than dT or CIA, showing that FaPydG is a lesion which retains the coding potential of dG. This is also in contrast to 8-oxodG, for which base pairing with dC and dA was established.