2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-methylgalactopyranose | 503551-13-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-methylgalactopyranose
• CAS: 503551-13-1
• 化学式: C₂₁H₂₅IO₅
• 分子量: 484.331
• InChiKey: GHZVXYINUSPEPM-IFLJBQAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-methylgalactopyranose 在 吡啶 、 4-二甲氨基吡啶 、 (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) 、 正丁基锂 、 二乙胺基三氟化硫 、 硫酸 、 10% Pd(OH)2/C 、 水 、 氢气 、 二正丁基氧化锡 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 57.08h， 生成 1-O-acetyl-2,3,6-tri-O-benzoyl-5-deoxy-5-fluoro-D-galactofuranose
  参考文献：
  名称：

  Fluorosugar Chain Termination Agents as Probes of the Sequence Specificity of a Carbohydrate Polymerase

  摘要：

  Naturally occurring carbohydrate polymers are ubiquitous. They are assembled by polymerizing glycosyltransferases, which can generate polysaccharide products with repeating sequence patterns. The fidelity of enzymes of this class is unknown. We report a method for testing the fidelity of carbohydrate polymerase pattern deposition: we synthesized fluorosugar donors and used them as chain termination agents. The requisite nucleotide fluorosugars could be produced from a single intermediate using the Jacobsen catalyst in a kinetically controlled separation of diastereomers. The resulting fluorosugar donors were used by the galactofuranosyltransferase GlfT2 from Mycobacterium tuberculosis, and the data indicate that this enzyme mediates the cell wall galactan production through a sequence-specific polymerization.

  DOI：

  10.1021/ja301723p
• 作为产物：
  描述：

  溴甲苯 在 咪唑 、 甲醇 、 碘 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-methylgalactopyranose
  参考文献：
  名称：

  Fluorosugar Chain Termination Agents as Probes of the Sequence Specificity of a Carbohydrate Polymerase

  摘要：

  Naturally occurring carbohydrate polymers are ubiquitous. They are assembled by polymerizing glycosyltransferases, which can generate polysaccharide products with repeating sequence patterns. The fidelity of enzymes of this class is unknown. We report a method for testing the fidelity of carbohydrate polymerase pattern deposition: we synthesized fluorosugar donors and used them as chain termination agents. The requisite nucleotide fluorosugars could be produced from a single intermediate using the Jacobsen catalyst in a kinetically controlled separation of diastereomers. The resulting fluorosugar donors were used by the galactofuranosyltransferase GlfT2 from Mycobacterium tuberculosis, and the data indicate that this enzyme mediates the cell wall galactan production through a sequence-specific polymerization.

  DOI：

  10.1021/ja301723p

文献信息

• Tsuji-Trost Reaction of Non-Derivatized Allylic Alcohols
  作者：Sunisa Akkarasamiyo、Supaporn Sawadjoon、Andreas Orthaber、Joseph S. M. Samec

  DOI：10.1002/chem.201705164

  日期：2018.3.7

  Palladium‐catalyzed allylic substitution of non‐derivatized enantioenriched allylic alcohols with a variety of uncharged N‐, S‐, C‐ and O‐centered nucleophiles using a bidentate BiPhePhos ligand is described. A remarkable effect of the counter ion (X) of the XPd[κ2‐BiPhePhos][η3‐C3H5] was observed. When ClPd[κ2‐BiPhePhos][η3‐C3H5] (complex I) was used as catalyst, non‐reproducible results were obtained

  描述了使用双齿BiPhePhos配体用各种不带电荷的N-，S-，C-和O-中心的亲核试剂对非衍生化对映体富集的烯丙醇进行钯催化的烯丙基取代。所述XPD [κ的抗衡离子（X）的一个显着的效果2 [η-BiPhePhos] 3 -C 3 H ^ 5 ]进行了观察。当CLPD [κ 2 -BiPhePhos] [η 3 -C 3 H ^ 5 ]（络合物 我）作为催化剂，得到的非可重复的结果。通过X射线晶体学研究络合物，31P NMR光谱，和ESI-MS显示发生了分解，其中亚磷酸酯配体的一种被氧化成相应的磷酸盐，产生CLPD [κ 1 -BiPhePhosphite磷酸] [η 3 -C 3 H ^ 5 ]种类（复合 II） 。当氯化物被交换成较弱的协调光学传递函数-离子更稳定的计数器的Pd [κ 2 -BiPhePhos] [η 3 -C 3 H ^ 5 ] + + [光学传递函数] - （络合