methyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-glucopyranoside
• 英文别名: methyl 6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside；Bz(-2)[Bz(-3)][Bz(-5)]D-Araf(a1-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Glc1Me；[(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]oxolan-2-yl]methyl benzoate
• 化学式: C₅₄H₅₂O₁₃
• 分子量: 908.999
• InChiKey: VLPNBYIASPVSFJ-RBZPXPGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  67
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  13

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl tri-O-benzoyl-α-D-arabinofuranoside	7473-42-9	C27H24O8	476.483
  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷	methyl 2,3,4-tri-O-benzyl-D-glucopyranoside	53008-65-4	C28H32O6	464.558
  ——	2,3,5-tri-O-benzoyl-D-arabinofuranosyl bromide	56271-35-3	C26H21BrO7	525.353

反应信息

• 作为产物：
  描述：

  methyl tri-O-benzoyl-α-D-arabinofuranoside 在 2,6-二甲基吡啶 、 甲醇 、 gold(III) chloride 、 乙酰溴 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Facile Synthesis of β- and α-Arabinofuranosides and Application to Cell Wall Motifs of M. tuberculosis

  摘要：

  Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.

  DOI：

  10.1021/ol400931p

文献信息

• The antituberculosis, antitumor, multibranched dodecafuranoarabinan of Mycobacterium species has been assembled from a single n-pentenylfuranoside source
  作者：Jun Lu、Bert Fraser-Reid

  DOI：10.1039/b413694b

  日期：——

  An n-pentenyl furanosyl-1,2-orthoester can function as a donor or be rearranged leading to an n-pentenyl furanoside acceptor which is glycosylated by its progenitor, regioselectively or doubly, thereby enabling rapid fabrication of a multibranched dodecasaccharide, known to possess a wide variety of biological interactions.

  一种 n-戊烯基呋喃糖-1,2-邻酯可以作为供体，或通过重排形成 n-戊烯基呋喃苷受体，该受体被其前体以区域选择性或双重方式糖基化，从而实现多支链十二糖的快速合成，该十二糖已知具有多种生物相互作用。
• Facile Synthesis of β- and α-Arabinofuranosides and Application to Cell Wall Motifs of <i>M. tuberculosis</i>
  作者：Shivaji A. Thadke、Bijoyananda Mishra、Srinivas Hotha

  DOI：10.1021/ol400931p

  日期：2013.5.17

  Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.