3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose | 410076-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose
• 英文别名: 3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-1,2-O-isopropylidene-β-L-threo-pentofuranose；1,2-O-isopropylidene-3-O-benzyl-bis(4,4-mesylmethyl)-α-D-glucofuranose；[(3aR,6R,6aR)-2,2-dimethyl-5-(methylsulfonyloxymethyl)-6-phenylmethoxy-6,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]methyl methanesulfonate
• CAS: 410076-92-5
• 化学式: C₁₈H₂₆O₁₀S₂
• 分子量: 466.53
• InChiKey: REPCZRIZHPZZRA-OAGGEKHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose 在 吡啶 、 18-冠醚-6 、 氨 、 四氯化锡 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 63.5h， 生成 (1S,3R,4S,7R)-1-(acetoxymethyl)-3-(6-N-benzoyladenin-9-yl)-7-benzyloxy-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  α-l-核糖构型锁定核酸 (α-L-LNA)：合成和性质

  摘要：

  单体核苷和 3'-O-亚磷酰胺结构单元的合成在生成 α-l-核糖构型锁核酸 (α-L-LNA) 的过程中，完全由 α-L-LNA 单体（α-l-核糖核酸）组成构型）或 α-L-LNA 和 DNA 单体的混合物（β-d-核糖构型），进行了描述，并研究了 α-L-LNA 低聚物。已制备双环 5-甲基胞嘧啶-1-基和腺嘌呤-9-基核苷衍生物，亚磷酰胺方法已用于自动寡聚化，从而产生 α-L-LNA 寡聚体。结合研究表明可以非常有效地识别单链 DNA 和 RNA 靶寡核苷酸链。因此，包含 α-L-LNA 单体和 DNA 单体混合物（“mix-mer α-L-LNA”）的立体不规则 α-L-LNA 11-mers 显示每次修改的 ΔTm 值为 +1 至 +3 °C与相应的未修饰 DNA·DNA 和 DNA·RNA 参考双链体相比，DNA 和 +4 至 +5°C 的 RNA。立体规则 f 每次修改的相应

  DOI：

  10.1021/ja0168763
• 作为产物：
  描述：

  3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 在 sodium hydroxide 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose
  参考文献：
  名称：

  An easy access to spiroannulated glyco-oxetane, -thietane and -azetane rings: synthesis of spironucleosides

  摘要：

  The key intermediate 11 derived from D-glucose and possessing bis-mesylmethyl (MsO center dot CH2-) functionality at C-4, was used to generate spirocycles 12, 13 and 15 via one-step procedures. The spirocompounds 12 and 13 were subsequently converted into the corresponding spironucleosides 24 and 26 in good yield using Vorbruggen reaction conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.175

文献信息

• Conformationally restricted triplex-forming oligonucleotides (TFOs). Binding properties of α-l-LNA and introduction of the N7-glycosylated LNA-guanosine
  作者：Alexei A. Koshkin

  DOI：10.1016/j.tet.2006.04.016

  日期：2006.6

  The method for scaled-up production of alpha-L-LNA phosphoramidite building blocks containing thymine and 5-methylcytosine nucleobases is described. Binding properties of pyrimidine TFOs modified with alpha-L-LNA are reported. In contrast to LNA TFOs, the fully modified a-L-LNA forms a stable triplex with a model DNA duplex. Pyrimidine DNA/LNA/alpha-L-LNA chimeras also efficiently hybridize with a model DNA duplex in the parallel mode. LNA nucleoside containing unnatural N-7-glycosylated guanine (LNA-(7) G) was synthesized by a convergent method and incorporated into LNA oligonucleotides. The triplex-forming alternating DNA/LNA oligonucleotides containing a single LNA-(7) G modification instead of internal LNA-mC demonstrate improved pH-dependent properties. The single LNA-(7) G modification can also discriminatively reduce competitive binding of TFOs to natural nucleic acids in the antiparallel duplex mode. (c) 2006 Elsevier Ltd. All rights reserved.
• SYNTHESIS OF A 2′-AMINO-α-L-LNA-T PHOSPHORAMIDITE
  作者：Patrick J. Hrdlicka、T. Santhosh Kumar、Jesper Wengel

  DOI：10.1080/15257770500276866

  日期：2005.4.1

  A convergent route to 2'-amino-alpha-L-LNA-T phosphoramidite building block 16 has been developed. Key steps include 1) introduction of a C2-azido group prior to nucleobase-coupling, 2) tandem Staudinger and intramolecular nucleophilic substitution reaction, and 3) separation of alpha-L- and beta-L-configured intermediates.
• α-<scp>l</scp>-<i>ribo</i>-Configured Locked Nucleic Acid (α-L-LNA):  Synthesis and Properties
  作者：Mads D. Sørensen、Lisbet Kværnø、Torsten Bryld、Anders E. Håkansson、Birgit Verbeure、Gilles Gaubert、Piet Herdewijn、Jesper Wengel

  DOI：10.1021/ja0168763

  日期：2002.3.1

  The syntheses of monomeric nucleosides and 3‘-O-phosphoramidite building blocks en route to α-l-ribo-configured locked nucleic acids (α-L-LNA), composed entirely of α-L-LNA monomers (α-l-ribo configuration) or of a mixture of α-L-LNA and DNA monomers (β-d-ribo configuration), are described and the α-L-LNA oligomers are studied. Bicyclic 5-methylcytosin-1-yl and adenin-9-yl nucleoside derivatives have

  单体核苷和 3'-O-亚磷酰胺结构单元的合成在生成 α-l-核糖构型锁核酸 (α-L-LNA) 的过程中，完全由 α-L-LNA 单体（α-l-核糖核酸）组成构型）或 α-L-LNA 和 DNA 单体的混合物（β-d-核糖构型），进行了描述，并研究了 α-L-LNA 低聚物。已制备双环 5-甲基胞嘧啶-1-基和腺嘌呤-9-基核苷衍生物，亚磷酰胺方法已用于自动寡聚化，从而产生 α-L-LNA 寡聚体。结合研究表明可以非常有效地识别单链 DNA 和 RNA 靶寡核苷酸链。因此，包含 α-L-LNA 单体和 DNA 单体混合物（“mix-mer α-L-LNA”）的立体不规则 α-L-LNA 11-mers 显示每次修改的 ΔTm 值为 +1 至 +3 °C与相应的未修饰 DNA·DNA 和 DNA·RNA 参考双链体相比，DNA 和 +4 至 +5°C 的 RNA。立体规则 f 每次修改的相应
• An easy access to spiroannulated glyco-oxetane, -thietane and -azetane rings: synthesis of spironucleosides
  作者：Ashim Roy、Basudeb Achari、Sukhendu B. Mandal

  DOI：10.1016/j.tetlet.2006.03.175

  日期：2006.6

  The key intermediate 11 derived from D-glucose and possessing bis-mesylmethyl (MsO center dot CH2-) functionality at C-4, was used to generate spirocycles 12, 13 and 15 via one-step procedures. The spirocompounds 12 and 13 were subsequently converted into the corresponding spironucleosides 24 and 26 in good yield using Vorbruggen reaction conditions. (c) 2006 Elsevier Ltd. All rights reserved.