2,3,5-Tri-O-benzyl-1-brom-D-arabinofuranose | 52492-41-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,5-Tri-O-benzyl-1-brom-D-arabinofuranose
• 英文别名: 2,3,5-Tri-O-benzyl-β-arabinofuranosyl Bromide；(2S,3S,4R,5R)-2-bromo-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane
• CAS: 52492-41-8
• 化学式: C₂₆H₂₇BrO₄
• 分子量: 483.402
• InChiKey: RNUQQVREQNIKHF-FXSWLTOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,5-Tri-O-benzyl-1-brom-D-arabinofuranose 、 磷酸二苄酯 生成 dibenzyl [(2S,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl] phosphate
  参考文献：
  名称：

  MARYANOFF, BRUCE E.;REITZ, ALLEN B.;NORTEY, SAMUEL O., TETRAHEDRON, 44,(1988) N 11, C. 3093-3106

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,5-Tri-O-benzyl-1-O-(p-nitrobenzoyl)-β-D-arabinofuranose 在 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 以98%的产率得到2,3,5-Tri-O-benzyl-1-brom-D-arabinofuranose
  参考文献：
  名称：

  Sugar derivatives of macrolides

  摘要：

  本发明涉及用于治疗移植抗拒、自身免疫疾病和真菌病的大环化合物的糖衍生物。

  公开号：

  US05747465A1

文献信息

• Stereoselective synthesis of β-arabino glycosyl sulfones as potential inhibitors of mycobacterial cell wall biosynthesis
  作者：Benjamin Ayers、Hilary Long、Edith Sim、Iain A. Smellie、Brendan L. Wilkinson、Antony J. Fairbanks

  DOI：10.1016/j.carres.2009.02.006

  日期：2009.4

  A series of beta-arabino glycosyl sulfones with varying alkyl chain lengths were synthesised in a stereoselective fashion as putative mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Biological testing against Mycobacterium bovis BCG revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which was maximal for a C-12 chain. (C) 2009 Elsevier Ltd. All rights reserved.
• Seela, Frank; Menkhoff, Sabine, Liebigs Annalen der Chemie, 1982, # 7, p. 1405 - 1408
  作者：Seela, Frank、Menkhoff, Sabine

  DOI：——

  日期：——
• Synthesis of 1′,2′-<i>cis</i>-Nucleoside Analogues: Evidence of Stereoelectronic Control for S_N2 Reactions at the Anomeric Center of Furanosides
  作者：Michel Prévost、Olivier St-Jean、Yvan Guindon

  DOI：10.1021/ja104429y

  日期：2010.9.8

  We are reporting a highly diastereoselective route to 1 ',2 '-cis-nucleoside analogues in the D-ribo, D-lyxo, D-xylo, and D-arabinoside series. Five-membered ring lactols undergo highly selective N-glycosidation reactions in the presence of dimethylboron bromide with different silylated nucleobases. Stereoelectronic control plays a crucial role for the observed induction, and the products are proposed to be formed through S(N)2 "exploded" transition states. This approach shows great potential considering its simplicity and selectivity for the synthesis of nucleoside analogues, an important class of molecules in medicinal chemistry.
• MARYANOFF, BRUCE E.;REITZ, ALLEN B.;NORTEY, SAMUEL O., TETRAHEDRON, 44,(1988) N 11, C. 3093-3106
  作者：MARYANOFF, BRUCE E.、REITZ, ALLEN B.、NORTEY, SAMUEL O.

  DOI：——

  日期：——
• SUGAR DERIVATIVES OF MACROLIDES
  申请人：PFIZER INC.

  公开号：EP0629209B1

  公开（公告）日：1997-05-14