benzyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranoside | 878288-82-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranoside
• 英文别名: (6aR,8S,9S,9aS)-8-phenylmethoxy-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-ol
• CAS: 878288-82-5
• 化学式: C₂₄H₄₂O₆Si₂
• 分子量: 482.765
• InChiKey: QLCNITCCGYKOEE-QPXUXIHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranoside 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 六氟异丙醇 、 四丁基氟化铵 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.75h， 生成 benzyl 2-O-benzyl-5-deoxy-5-[2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-episulfoniumylidene-D-arabinitol]-3-O-sulfoxy-α-D-arabinofuranose inner salt
  参考文献：
  名称：

  Synthesis of Sulfonium Sulfate Analogues of Disaccharides and Their Conversion to Chain-Extended Homologues of Salacinol: New Glycosidase Inhibitors

  摘要：

  [graphics]Four chain extended homologues of salacinol, a naturally occurring glycosidase inhibitor, were prepared for evaluation as inhibitors of glucosidase enzymes involved in the breakdown of carbohydrates. The syntheses involved the reactions of 1,4-anhydro-2,3,5-tri-O-benzyl-4-thiO-D-arabinitol with cyclic sulfate derivatives of different monosaccharides. Debenzylation of the products afforded the novel sulfonium sulfate derivatives Of D-glucose, D-galactose, D-arabinose, and D-Xylose that are of interest in their own right as glycosidase inhibitors. Reduction to the corresponding alditols then afforded the homologues of salacinol containing polyhydroxylated, acyclic chains of 5- and 6-carbons, differing in stereochemistry at the stereogenic centers. Three of the chain-extended homologues inhibited recombinant human maltase glucoamylase, one of the key intestinal enzymes involved in the breakdown of glucose oligosaccharides in the sinall intestine, with K-i values in the low microinolar range, of approximately the saine inagnitude as salacinol, thus providing lead candidates for the treatment of Type 2 diabetes.

  DOI：

  10.1021/jo052252u
• 作为产物：
  描述：

  benzyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 在 吡啶 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 benzyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of Sulfonium Sulfate Analogues of Disaccharides and Their Conversion to Chain-Extended Homologues of Salacinol: New Glycosidase Inhibitors

  摘要：

  [graphics]Four chain extended homologues of salacinol, a naturally occurring glycosidase inhibitor, were prepared for evaluation as inhibitors of glucosidase enzymes involved in the breakdown of carbohydrates. The syntheses involved the reactions of 1,4-anhydro-2,3,5-tri-O-benzyl-4-thiO-D-arabinitol with cyclic sulfate derivatives of different monosaccharides. Debenzylation of the products afforded the novel sulfonium sulfate derivatives Of D-glucose, D-galactose, D-arabinose, and D-Xylose that are of interest in their own right as glycosidase inhibitors. Reduction to the corresponding alditols then afforded the homologues of salacinol containing polyhydroxylated, acyclic chains of 5- and 6-carbons, differing in stereochemistry at the stereogenic centers. Three of the chain-extended homologues inhibited recombinant human maltase glucoamylase, one of the key intestinal enzymes involved in the breakdown of glucose oligosaccharides in the sinall intestine, with K-i values in the low microinolar range, of approximately the saine inagnitude as salacinol, thus providing lead candidates for the treatment of Type 2 diabetes.

  DOI：

  10.1021/jo052252u

文献信息

• Control of α/β Anomer Formation by a 2′,5′ Bridge: Toward Nucleoside Derivatives Locked in the South Conformation
  作者：Hubert Hřebabecký、Martin Dračínský、Eliška Procházková、Michal Šála、Richard Mackman、Radim Nencka

  DOI：10.1021/acs.joc.7b01000

  日期：2017.11.3

  We describe a novel stereoselective synthesis of nucleoside derivatives with the ribose ring locked in the South conformation by a bridge between C2′ and C5′. Despite the intrinsic constraints of the bicyclic structure, we demonstrate that their synthesis can be achieved by ring closing metathesis of readily accessible precursors. The obtained ribose derivatives are, however, very poor substrates for

  我们描述了核苷衍生物的新型立体选择性合成，其核糖环通过C2'和C5'之间的桥锁定在South构象中。尽管存在双环结构的固有限制，但我们证明了它们的合成可以通过容易获得的前体的闭环复分解来实现。然而，获得的核糖衍生物是用于进一步安装核碱基的非常差的底物，甚至简单的亲核试剂，例如叠氮基或氰基阴离子，在标准糖基化条件下也会与意想不到的立体选择性或区域选择性反应。在这里，我们通过采用密度泛函理论（DFT）计算来解释这种行为，并设计出一种替代方法，使异构体具有所需的核碱基方向。
• Synthesis of Sulfonium Sulfate Analogues of Disaccharides and Their Conversion to Chain-Extended Homologues of Salacinol: New Glycosidase Inhibitors
  作者：Blair D. Johnston、Henrik H. Jensen、B. Mario Pinto

  DOI：10.1021/jo052252u

  日期：2006.2.1

  [graphics]Four chain extended homologues of salacinol, a naturally occurring glycosidase inhibitor, were prepared for evaluation as inhibitors of glucosidase enzymes involved in the breakdown of carbohydrates. The syntheses involved the reactions of 1,4-anhydro-2,3,5-tri-O-benzyl-4-thiO-D-arabinitol with cyclic sulfate derivatives of different monosaccharides. Debenzylation of the products afforded the novel sulfonium sulfate derivatives Of D-glucose, D-galactose, D-arabinose, and D-Xylose that are of interest in their own right as glycosidase inhibitors. Reduction to the corresponding alditols then afforded the homologues of salacinol containing polyhydroxylated, acyclic chains of 5- and 6-carbons, differing in stereochemistry at the stereogenic centers. Three of the chain-extended homologues inhibited recombinant human maltase glucoamylase, one of the key intestinal enzymes involved in the breakdown of glucose oligosaccharides in the sinall intestine, with K-i values in the low microinolar range, of approximately the saine inagnitude as salacinol, thus providing lead candidates for the treatment of Type 2 diabetes.