1,2-O-isopropylidene-5-triisopropylsilyl-D-xylofuranose | 257277-43-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-5-triisopropylsilyl-D-xylofuranose
• 英文别名: (3aR,5R,6S,6aR)-2,2-dimethyl-5-[tri(propan-2-yl)silyloxymethyl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 257277-43-3
• 化学式: C₁₇H₃₄O₅Si
• 分子量: 346.539
• InChiKey: BXIAODHSVAOMGV-QKPAOTATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-5-triisopropylsilyl-D-xylofuranose 在 吡啶 、 sodium tetrahydroborate 、 sodium azide 、 草酰氯 、 四丁基氟化铵 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 [(3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of functionalized cyclohexenephosphonates and their inhibitory activity towards bacterial sialidases

  摘要：

  We have synthesized a series of cyclohexenephosphonates derived from D- and L-xylose, designed as core structures for the development of high affinity mimics of sialic acid and of the sialidase reaction transition state, Extension of our syntheses to both xylose enantiomers has given us access to two series of cyclohexenephosphonates with regioisomeric double bonds. We have demonstrated the selective functionalization of the hydroxyl groups towards introduction of a glycerol side chain mimic and immobilization via a silyl linker. The inhibitory activity of a selected set of compounds towards three bacterial sialidases has been tested and moderate activity was found. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00873-6
• 作为产物：
  描述：

  [(3aR,5R,6S,6aR)-2,2-dimethyl-6-triethylsilyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methoxy-tri(propan-2-yl)silane 在 三氯化铁 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以88%的产率得到1,2-O-isopropylidene-5-triisopropylsilyl-D-xylofuranose
  参考文献：
  名称：

  Facile Cleavage of Silyl Protecting Groups with Catalytic Amounts of FeCl₃

  摘要：

  本文介绍了一种温和且环境友好的方法，使用催化量的铁离子在甲醇中去除硅烷保护基团。该方法特别有效地裂解了三乙基硅烷（TES）保护基团。

  DOI：

  10.1055/s-2006-926256

文献信息

• A new approach for the synthesis of 3′-deoxy-3′-C-formyl-ribonucleosides and the synthesis of alternating methylene(methylimino) linked phosphodiester backbone oligonucleotides with 2′-OH and 2′-OMe groups
  作者：Marija Prhavc、George Just*、Balkrishen Bhat、P.Dan Cook、Muthiah Manoharan

  DOI：10.1016/s0040-4039(00)01814-1

  日期：2000.12

  A stereoselective synthesis of 3'-deoxy-3'-C-formyl-5-methyluridine 2 is described via the dithiane 4 as the key intermediate. Compound 2 was coupled with 3 into a novel ribo-MMI dimer 1. The dimer was then incorporated into antisense oligonucleotides which were found to have high binding affinity to the target RNA. (C) 2000 Elsevier Science Ltd. All rights reserved.
• CHIMERIC RNA WITH MODIFIED BACKBONES: ALTERNATING METHYLENE(METHYLIMINO) LINKED PHOSPHODIESTER BACKBONE OLIGONUCLEOTIDES WITH 2′-OH AND 2′-OMe GROUPS
  作者：Marija Prhavc、Balkrishen Bhat、George Just、P. Dan Cook、Muthiah Manoharan

  DOI：10.1081/ncn-100002476

  日期：2001.3.31

  Synthesis of a novel ribo-MMI dimer with 2'-OH and 2'-OMe in 5'- and 3'-nucleosides, respectively is presented. The synthesis was accomplished by reductive coupling of 3'-deoxy-3'-C-formyluridine and 2'-O-methyl-5'-O-methylaminouridine via a thioacetal as the key intermediate for the top part of the dimer. Incorporation of ribo-MMI dimers into oligonucleotides increased binding affinity for target RNA.
• Facile Cleavage of Silyl Protecting Groups with Catalytic Amounts of FeCl₃
  作者：Yikang Wu、Yong-Qing Yang、Jia-Rong Cui、Lin-Gui Zhu、Ya-Ping Sun

  DOI：10.1055/s-2006-926256

  日期：——

  A very mild and environmentally benign method for ­removal of silyl protecting groups using catalytic amounts of iron ion in MeOH is presented. The method is particularly effective for cleaving triethylsilyl (TES) protecting groups.

  本文介绍了一种温和且环境友好的方法，使用催化量的铁离子在甲醇中去除硅烷保护基团。该方法特别有效地裂解了三乙基硅烷（TES）保护基团。
• Synthesis of functionalized cyclohexenephosphonates and their inhibitory activity towards bacterial sialidases
  作者：Hansjörg Streicher、Christoph Bohner

  DOI：10.1016/s0040-4020(02)00873-6

  日期：2002.9

  We have synthesized a series of cyclohexenephosphonates derived from D- and L-xylose, designed as core structures for the development of high affinity mimics of sialic acid and of the sialidase reaction transition state, Extension of our syntheses to both xylose enantiomers has given us access to two series of cyclohexenephosphonates with regioisomeric double bonds. We have demonstrated the selective functionalization of the hydroxyl groups towards introduction of a glycerol side chain mimic and immobilization via a silyl linker. The inhibitory activity of a selected set of compounds towards three bacterial sialidases has been tested and moderate activity was found. (C) 2002 Elsevier Science Ltd. All rights reserved.