3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-methyl-β-D-ribofuranos-1-yl trichloroacetamide | 166593-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-methyl-β-D-ribofuranos-1-yl trichloroacetamide
• 英文别名: [(6aR,8S,9R,9aR)-9-methoxy-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] 2,2,2-trichloroethanimidate
• CAS: 166593-39-1
• 化学式: C₂₀H₃₈Cl₃NO₆Si₂
• 分子量: 551.055
• InChiKey: UEGVBCOTPZOSIK-TVFCKZIOSA-N

物化性质

• 沸点：
  449.2±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-methyl-β-D-ribofuranos-1-yl trichloroacetamide 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 0.08h， 生成 N-(1-{(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-methoxy-tetrahydro-furan-2-yl}-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide
  参考文献：
  名称：

  Efficient synthesis of 2′-O-alkyl ribonucleosides using trichloroacetimidate d-ribofuranosides as ribosyl donors

  摘要：

  Trichloroacetimidate-2-O-alkyl-3, 5-O-TIPS-beta-D-ribofuranoside glycosylates silylated nucleobases in a fast high-yielding and stereoselective reaction promoted by trimethylsilyl trifluoromethanesulfonate. This method has been applied to the synthesis of 2'-O-alkyl ribonucleosides further transformed to building blocks ready for oligo(2'-O-alkyl)ribonucleotide construction.

  DOI：

  10.1016/s0040-4039(00)75987-9
• 作为产物：
  描述：

  (6aR,8R,9R,9aR)-8-(benzyloxy)-2,2,4,4-tetraisopropyl-9-methoxytetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocine 在 palladium on activated charcoal 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 生成 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-methyl-β-D-ribofuranos-1-yl trichloroacetamide
  参考文献：
  名称：

  Efficient synthesis of 2′-O-alkyl ribonucleosides using trichloroacetimidate d-ribofuranosides as ribosyl donors

  摘要：

  Trichloroacetimidate-2-O-alkyl-3, 5-O-TIPS-beta-D-ribofuranoside glycosylates silylated nucleobases in a fast high-yielding and stereoselective reaction promoted by trimethylsilyl trifluoromethanesulfonate. This method has been applied to the synthesis of 2'-O-alkyl ribonucleosides further transformed to building blocks ready for oligo(2'-O-alkyl)ribonucleotide construction.

  DOI：

  10.1016/s0040-4039(00)75987-9

文献信息

• Detailed Studies on Trimethylselyl Triflate Mediated Glycosylation<i>via</i>a 3,5-<i>O</i>-(l,l,3,3-Tetraisopropyl-Disiloxane-l,3-diyl)-2-<i>O</i>-methylribofuranos-l-yl Trichloroacetimidate Intermediate
  作者：Koh-ichiroh Shohda、Takeshi Wada、Mitsuo Sekine

  DOI：10.1080/07328319808004310

  日期：1998.12

  The reaction of 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-methylribofuranos-1-yl trichloroacetimidate as the ribosyl donor with bis(trimethylsilyl)thymine was studied in detail. As the result, it was concluded that the main product is an alpha-glycoside derivative unlike the previous report. In connection with this glycosylation, several chemical properties of the byproduct obtained by the Chapman rearrangement are described.
• Efficient synthesis of 2′-O-alkyl ribonucleosides using trichloroacetimidate d-ribofuranosides as ribosyl donors
  作者：Luc Chanteloup、Nguyen t. Thuong

  DOI：10.1016/s0040-4039(00)75987-9

  日期：1994.1

  Trichloroacetimidate-2-O-alkyl-3, 5-O-TIPS-beta-D-ribofuranoside glycosylates silylated nucleobases in a fast high-yielding and stereoselective reaction promoted by trimethylsilyl trifluoromethanesulfonate. This method has been applied to the synthesis of 2'-O-alkyl ribonucleosides further transformed to building blocks ready for oligo(2'-O-alkyl)ribonucleotide construction.