2,3,5-tri-O-benzoyl-1-O-benzyl-β-D-ribofuranose | 59556-69-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-benzoyl-1-O-benzyl-β-D-ribofuranose
• 英文别名: benzyl 2,3,5-tri-O-benzoyl-β-D-ribofuranoside；benzyl-(tri-O-benzoyl-β-D-ribofuranoside)；Benzyl-(tri-O-benzoyl-β-D-ribofuranosid)；Benzyl beta-d-ribofuranoside tribenzoate；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-phenylmethoxyoxolan-2-yl]methyl benzoate
• CAS: 59556-69-3
• 化学式: C₃₃H₂₈O₈
• 分子量: 552.581
• InChiKey: YTXMDSQXQRTXIM-OZLMZZSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzoyl-1-O-benzyl-β-D-ribofuranose 在 吡啶 、 palladium(II) oxide 、 calcium sulfate 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 、 溴化钛(IV) 、 二正丁基氧化锡 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 72.17h， 生成 3-O-acetyl-5-O-benzoyl-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-D-ribofuranosyl bromide
  参考文献：
  名称：

  含有d-核糖和3-deoxy-d-manno-2-octulosonic酸（KDO）的大肠杆菌荚膜多糖重复单元的合成

  摘要：

  摘要寡糖，（3-脱氧-7-O-β-d-呋喃核糖基-β-d-甘露糖-2-辛基吡喃糖苷）钠，2- O-β-d-呋喃核糖基-β-d-呋喃呋喃糖苷，并从其中制备异头[甲基3-脱氧-7-O-（2-O-β-d-核呋喃糖基-β-d-核呋喃呋喃糖基）-α-和-β-d-甘露糖-2-辛基吡喃葡萄糖苷]。 1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-d-核呋喃糖和异头甲基（甲基8-O-苄基-4,5-O-羰基-3-脱氧-α-和-β-d-甘露糖-2-辛基吡喃葡萄糖苷，纯度高，总收率令人满意。它们构成了第一系列模型化合物，用于光谱和免疫化学研究大肠杆菌菌株LP 1092和K 23的荚膜多糖。必不可少的糖苷间键[β-d -Rib f-（1→7）-α-或- β-d -dOclA，和β-d-Ribf-（（1→2）-β-d-Ribf]通过使用适当的d-核呋喃糖基溴化物衍生物的三氟甲磺酸银方法的修饰而形成。组成和构型分配基于寡糖的受保护衍生物的250-MHz

  DOI：

  10.1016/0008-6215(84)85223-4
• 作为产物：
  描述：

  D-核糖 在 吡啶 、 盐酸 作用下， 生成 2,3,5-tri-O-benzoyl-1-O-benzyl-β-D-ribofuranose
  参考文献：
  名称：

  New Benzoyl Derivatives of D-Ribofuranose and aldehydo-D-Ribose. The Preparation of Crystalline 2,3,5-Tri-O-benzoyl-β-D-ribose from D-Ribose¹

  摘要：

  DOI：

  10.1021/ja01632a038

文献信息

• Synthesis of alkylcarbonate analogs of O-acetyl-ADP-ribose
  作者：Marcela Dvorakova、Radim Nencka、Milan Dejmek、Eva Zbornikova、Anna Brezinova、Marie Pribylova、Radek Pohl、Marie E. Migaud、Tomas Vanek

  DOI：10.1039/c3ob41016a

  日期：——

  The non-hydrolyzable alkylcarbonate analogs of O-acetyl-ADP-ribose have been synthesized from the phosphorylated ribose derivatives after coupling with AMP morpholidate promoted by mechanical grinding. The analogs were assessed for their ability to inhibit the human sirtuin homolog SIRT1.

  在机械研磨的促进下，O-乙酰基-ADP-核糖与 AMP 吗啉烷酸酯偶联，从磷酸化核糖衍生物中合成了不可水解的烷基碳酸酯类似物。对这些类似物抑制人类 sirtuin 同源物 SIRT1 的能力进行了评估。
• A one-pot glycosylation of tetrahydropyranyl (THP) ether intermediates
  作者：Stefano Manfredini、Pier G. Baraldi、Rita Bazzanini、Mario Guarneri、Daniele Simoni

  DOI：10.1016/s0040-4039(00)77285-6

  日期：1994.8

  Tetrahydropyranyl (THP) derivatives of alcohols are converted in one-pot and in stereoselective manner into the corresponding 1-O-alkyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosides on treatment with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose and trimethylsilyl triflate (TMSOTf). The same protocol was also applyed on 1-O-acetyl-2,3,4,6-tetra-O-benzyl-glucopyranoside (α/β 9:1) to give, by reaction with

  四氢吡喃基（THP）醇的衍生物被转换在单罐和立体选择性的方式将相应的1- ø -烷基-2,3,5-三ö治疗苯甲酰基β-d-ribofuranosides与1- ö -乙酰-2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖和三氟甲磺酸三甲基甲硅烷基酯（TMSOTf）。对1 - O-乙酰基-2,3,4,6-四-O-苄基-吡喃葡萄糖苷（α/β9：1）也应用相同的方案，通过与1 - O-甲基-2反应，得到3，4-三-O-苄基-6-THP-α-D-吡喃葡萄糖苷，相应的二糖胺（α/β3：1）。该反应收率高，并且在非常温和的条件下（-30°C）使用容易获得的起始原料快速进行。
• Gold(III)-Catalyzed Glycosidations for 1,2-<i>trans</i> and 1,2-<i>cis</i> Furanosides
  作者：Shivaji A. Thadke、Bijoyananda Mishra、Srinivas Hotha

  DOI：10.1021/jo501052y

  日期：2014.8.15

  Stereoselective synthesis of furanosides is still a daunting task, unlike the pyranosides, for which several methods exist. Herein, a unified stereoselective strategy for the synthesis of 1,2-trans and 1,2-cis furanosides is revealed for seven out of eight possible isomers of pentoses. The identified protocol gives access to diastereoselective synthesis of α- and β-araf, ribf, lyxf, and α-xylf furanosides. 1,2-trans glycosides were synthesized by the use of propargyl 1,2-orthoesters under gold-catalyzed glycosidation conditions, and subsequently, they are converted into 1,2-cis glycosides through oxidation-reduction as the key functional group transformation. All the reactions are found to be fully diastereoselective, mild, and high yielding.
• Highly Efficient <i>O</i>-Glycosylations with <i>p</i>-Tolyl Thioribosides and <i>p</i>-TolSOTf
  作者：Michio Kurosu、Kai Li

  DOI：10.1021/jo801408x

  日期：2008.12.19

  GraphicsA wide variety of p-tolyl thioriboside donors are examined for O-ribosylations of primary and secondary alcohols. p-Tolylsulfenyl trifluoromethanesulfonate (p-TolSOTf) is very effective in promoting O-ribosylations with p-tolyl thioriboside; all reactions are completed within 1-15 min to provide the desired products in good yield with reliable alpha/beta selectivity. A wide range of functional groups are tolerated under these conditions. The described O-ribosylation conditions are very useful for the generation of ribosaminouridine library molecules in solution or on polymer support.
• Syntheses of repeating units of Escherichia coli capsular polysaccharides containing d-ribose and 3-deoxy-d-manno-2-octulosonic acid (KDO)
  作者：Paul Kosma、Gerhard Schulz、Frank M. Unger

  DOI：10.1016/0008-6215(84)85223-4

  日期：1984.9

  -2-octulopyranosid)onate in high purity and in acceptable over-all yields. They constitute a first series of model compounds for spectroscopic and immunochemical studies of the capsular polysaccharides from Escherichia coli strains LP 1092 and K 23. The essential, interglycosidic linkages [β- d -Rib f -(1→7)-α- or -β- d -dOclA, and β- d -Rib f -(1→2)-β- d -Rib f ] were formed by a modification of the

  摘要寡糖，（3-脱氧-7-O-β-d-呋喃核糖基-β-d-甘露糖-2-辛基吡喃糖苷）钠，2- O-β-d-呋喃核糖基-β-d-呋喃呋喃糖苷，并从其中制备异头[甲基3-脱氧-7-O-（2-O-β-d-核呋喃糖基-β-d-核呋喃呋喃糖基）-α-和-β-d-甘露糖-2-辛基吡喃葡萄糖苷]。 1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-d-核呋喃糖和异头甲基（甲基8-O-苄基-4,5-O-羰基-3-脱氧-α-和-β-d-甘露糖-2-辛基吡喃葡萄糖苷，纯度高，总收率令人满意。它们构成了第一系列模型化合物，用于光谱和免疫化学研究大肠杆菌菌株LP 1092和K 23的荚膜多糖。必不可少的糖苷间键[β-d -Rib f-（1→7）-α-或- β-d -dOclA，和β-d-Ribf-（（1→2）-β-d-Ribf]通过使用适当的d-核呋喃糖基溴化物衍生物的三氟甲磺酸银方法的修饰而形成。组成和构型分配基于寡糖的受保护衍生物的250-MHz