1,2-O-isopropylidene-3,5-di-O-(trifluoromethanesulfonyl)-α-D-ribofuranose | 250130-88-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1,2-O-isopropylidene-3,5-di-O-(trifluoromethanesulfonyl)-α-D-ribofuranose
• 英文别名: [(3aR,5R,6R,6aR)-2,2-dimethyl-6-(trifluoromethylsulfonyloxy)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl trifluoromethanesulfonate
• CAS: 250130-88-2
• 化学式: C₁₀H₁₂F₆O₉S₂
• 分子量: 454.322
• InChiKey: UKSLJPCNRILSRN-DBRKOABJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3,5-di-O-(trifluoromethanesulfonyl)-α-D-ribofuranose 在 sodium tetrahydroborate 、 水 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 66.0h， 生成 N-benzyl-1,3-dideoxy-1,3-imino-L-xylitol
  参考文献：
  名称：

  Inhibition of Nonmammalian Glycosidases by Azetidine Iminosugars Derived from Stable 3,5-Di-O-triflates of Pentoses

  摘要：

  Efficient ring closure of stable crystalline 3,5-dl-O-triflates of pentofuranosides with amines to form azetidines allowed preliminary evaluation of four-ring iminosugars as glycosidase inhibitors; significant and specific inhibition of nonmammallan alpha-glucosidases Is shown by L-xylo- and L-arabino-iminosugar azetidines.

  DOI：

  10.1021/ol2024482
• 作为产物：
  描述：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 重铬酸吡啶 、 乙醇 、 水 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1,2-O-isopropylidene-3,5-di-O-(trifluoromethanesulfonyl)-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis of Different 3,5‐Diazidofuranoses: A New and General Synthesis Pathway

  摘要：

  Diamino- and diazidofuranoses represent useful precursors, for example, for the synthesis of substituted nucleosides and metal complexes, respectively. Known procedures for their synthesis lack the availability of cheap starting materials, adequate yields, and the access to all possible diastereomeres. Therefore, 3,5-diazido-3,5-dideoxy- and - 2,3,5- trideoxyfuranoses both with ribo- and xylo- configuration were prepared using different approaches.

  DOI：

  10.1080/07328300701540175

文献信息

• Synthesis of Rh(I) and Ir(I) metal complexes with the first two chiral dithiolate ligands derived from carbohydrates
  作者：Oscar Pàmies、Gemma Net、Aurora Ruiz、Carles Bo、Josep Maria Poblet、Carmen Claver

  DOI：10.1016/s0022-328x(99)00251-x

  日期：1999.9

  olefinic Rh(I) and Ir(I) complexes [M2(μ-RiSS)(cod)2] (M=Rh 1, Ir 3) and [M2(μ-XySS)(cod)2] (M=Rh 2, Ir 4) were synthesized and characterized. The Rh(I) complexes reacted with CO to give the corresponding binuclear tetracarbonyls [Rh2(μ_RiSS)(CO)4] (5) and [Rh2(μ-XySS)(CO)4] (6), which reacted with two equivalents of PPh3 to form mixed carbonyl-phosphine complexes [Rh2(μ-RiSS)(CO)2(PPh3)2] (7) and

  新的手性二硫醇化合物1,2-O-异亚丙基-3,5-二硫醇-α-d-呋喃核糖RiSSH 2和1,2-O-异亚丙基-3,5-二硫醇-α-d-木呋喃糖XySSH 2及其手性二硫代烯烃Rh（I）和Ir（I）配合物[M 2（μ-RiSS）（cod）2 ]（M = Rh 1，Ir 3）和[M 2（μ-XySS）（cod）2 ]（M合成并表征Rh 2，Ir 4）。上的Rh（I）络合物与CO反应，得到相应的双核tetracarbonyls的[Rh 2（μ _ RISS）（CO）4 ]（5）和铑[Rh 2（μ-XySS）（CO）4 ]（6），其与两个当量的PPh 3反应形成混合的羰基膦复合物[Rh 2（μ-RiSS）（CO）2（PPh 3）2 ]（7）和[Rh 2（μ-XySS） ）（CO）2（PPh 3）2 ]（8）。[Rh 2（μ-RiSS）（CO）4 ]（5）的结构以及[Rh 2（μ-XySS）（CO）4
• Synthesis of palladium(ii) complexes containing a new α-d-xylofuranose-modified diphosphine and their application as catalyst precursors in the co- and terpolymerization of CO–ethene and propene
  作者：Bianca K. Muñoz-Moreno、Carmen Claver、Aurora Ruiz、Claudio Bianchini、Andrea Meli、Werner Oberhauser

  DOI：10.1039/b719748a

  日期：——

  The diphosphine 3,5-dideoxy-1,2-O-isopropylidene-3,5-bis(di(2-methoxyphenyl)phosphanyl)-α-D-xylofuranose (o-MeO-xylophos), which differs from the known 3,5-dideoxy-1,2-O-isopropylidene-3,5-bis(diphenylphosphanyl)-α-D-xylofuranose (xylophos) by the presence of 2-methoxy substituents on the P-aryl rings, has been synthesized and characterized. These two ligands have been employed to stabilize the PdII complexes [PdCl2(o-MeO-xylophos)] (1a), [PdCl2(xylophos)] (2a), [PdClMe(o-MeO-xylophos)] (1b), [PdClMe(xylophos)] (2b), [Pd(OTs)(H2O)(o-MeO-xylophos)](OTs) (1c) and [Pd(OTs)(H2O)(xylophos)](OTs) (2c). All complexes have been characterized by multinuclear-NMR spectroscopy. The solid-state structure of 1a has been determined by a single crystal X-ray analysis. The Pd–aqua complexes 1c and 2c have been employed to catalyse the CO–ethene and CO–propene copolymerization as well as the CO–ethene–propene terpolymerization reaction in MeOH. The catalytic activity and the molecular weight of the polyketones have been compared to those of the products obtained with analogous catalysts, [Pd(H2O)2(o-MeO-dppp)](OTs)2 (3c) and [Pd(H2O)(OTs)(dppp)](OTs) (4c), bearing the classical 1,3-bis(diphenylphoshino)propane ligand (dppp). Under comparable catalytic conditions, all catalysts produce structurally similar polymeric materials, with 1c yielding the largest propene incorporation as well as the highest productivity of low-molecular-weight terpolymers.

  3,5-二脱氧-1,2-O-异亚丙基-3,5-双(二(2-甲氧基苯基)膦酰基)-δ-D-氧基呋喃糖(邻甲氧基木磷)与已知的3,5-二脱氧-1、2-O-isopropylidene-3,5-bis(diphenylphosphanyl)-α-D-xylofuranose (xylophos)的不同之处在于其 P-芳基环上存在 2-甲氧基取代基。这两种配体被用来稳定 PdII 复合物 [PdCl2(o-MeO-xylophos)] (1a)、[PdCl2(xylophos)] (2a)、[PdClMe(o-MeO-xylophos)] (1b)、[PdClMe(xylophos)] (2b)、[Pd(OTs)(H2O)(o-MeO-xylophos)](OTs) (1c) 和 [Pd(OTs)(H2O)(xylophos)](OTs)(2c)。所有配合物都通过多核核磁共振光谱进行了表征。单晶 X 射线分析确定了 1a 的固态结构。钯水配合物 1c 和 2c 被用于催化一氧化碳与一氧化碳与丙烯的共聚以及一氧化碳与丙烯在 MeOH 中的三元共聚反应。聚酮的催化活性和分子量与使用类似催化剂[Pd(H2O)2(o-MeO-dppp)](OTs)2 (3c)和[Pd(H2O)(OTs)(dppp)](OTs)(4c)得到的产物的分子量进行了比较，这两种催化剂都带有经典的 1,3-双（二苯基樟脑）丙烷配体（dppp）。在相似的催化条件下，所有催化剂都能生成结构相似的聚合物材料，其中 1c 生成的丙烯掺杂量最大，低分子量三元共聚物的生产率也最高。
• A New Diphosphane Derived from Carbohydrates as an Effective Ligand for Asymmetric Hydrogenation
  作者：Oscar Pàmies、Gemma Net、Aurora Ruiz、Carmen Claver

  DOI：10.1002/1099-0682(200009)2000:9<2011::aid-ejic2011>3.0.co;2-#

  日期：2000.9
• Inhibition of Nonmammalian Glycosidases by Azetidine Iminosugars Derived from Stable 3,5-Di-<i>O</i>-triflates of Pentoses
  作者：Gabriel M. J. Lenagh-Snow、Noelia Araujo、Sarah F. Jenkinson、Catherine Rutherford、Shinpei Nakagawa、Atsushi Kato、Chu-Yi Yu、Alexander C. Weymouth-Wilson、George W. J. Fleet

  DOI：10.1021/ol2024482

  日期：2011.11.4

  Efficient ring closure of stable crystalline 3,5-dl-O-triflates of pentofuranosides with amines to form azetidines allowed preliminary evaluation of four-ring iminosugars as glycosidase inhibitors; significant and specific inhibition of nonmammallan alpha-glucosidases Is shown by L-xylo- and L-arabino-iminosugar azetidines.
• Synthesis of Different 3,5‐Diazidofuranoses: A New and General Synthesis Pathway
  作者：Daniel Koth、Andrea Fiedler、Sandy Scholz、Michael Gottschaldt

  DOI：10.1080/07328300701540175

  日期：2007.9

  Diamino- and diazidofuranoses represent useful precursors, for example, for the synthesis of substituted nucleosides and metal complexes, respectively. Known procedures for their synthesis lack the availability of cheap starting materials, adequate yields, and the access to all possible diastereomeres. Therefore, 3,5-diazido-3,5-dideoxy- and - 2,3,5- trideoxyfuranoses both with ribo- and xylo- configuration were prepared using different approaches.