5-O-acetyl-2,3-di-O-benzyl-α-D-arabinofuranosyl chloride | 121604-11-3

• 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: 5-O-acetyl-2,3-di-O-benzyl-α-D-arabinofuranosyl chloride
• 英文别名: [(2R,3R,4S,5R)-5-chloro-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl acetate
• CAS: 121604-11-3
• 化学式: C₂₁H₂₃ClO₅
• 分子量: 390.864
• InChiKey: FJDNXXVZTLYKFY-CGXNFDGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-acetyl-2,3-di-O-benzyl-α-D-arabinofuranosyl chloride 在 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R)-3,4-bis-benzyloxy-5-octyloxy-tetrahydro-furan-2-ylmethoxy)-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Synthesis of oligosaccharide fragments of mannosylated lipoarabinomannan from Mycobacterium tuberculosis

  摘要：

  The synthesis of three mannosyl-arabinosides 4-6 found as terminal epitopes of mannosylated lipoarabinomannan (ManLAM) from Mycobacterium tuberculosis is reported. A key step in the synthesis of the required protected octyl beta-D-arabinofuranoside derivative 7 involved glycosylation of octanol by 5-O-acetyl-2,3-di-O-benzyl-alpha-D-arabinofuranosyl chloride (12) in the absence of a promoter. The sequential addition of the mannopyranose residues to 7, using thioglycosides 8 and 9, provided the protected oligosaccharides 17, 19, and 21. Deprotection by deacylation and then hydrogenation afforded the targets. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00260-4
• 作为产物：
  描述：

  1,5-di-O-acetyl-2,3-di-O-benzyl-D-arabinofuranose 在 盐酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.17h， 生成 5-O-acetyl-2,3-di-O-benzyl-α-D-arabinofuranosyl chloride
  参考文献：
  名称：

  Synthesis of oligosaccharide fragments of mannosylated lipoarabinomannan from Mycobacterium tuberculosis

  摘要：

  The synthesis of three mannosyl-arabinosides 4-6 found as terminal epitopes of mannosylated lipoarabinomannan (ManLAM) from Mycobacterium tuberculosis is reported. A key step in the synthesis of the required protected octyl beta-D-arabinofuranoside derivative 7 involved glycosylation of octanol by 5-O-acetyl-2,3-di-O-benzyl-alpha-D-arabinofuranosyl chloride (12) in the absence of a promoter. The sequential addition of the mannopyranose residues to 7, using thioglycosides 8 and 9, provided the protected oligosaccharides 17, 19, and 21. Deprotection by deacylation and then hydrogenation afforded the targets. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00260-4

文献信息

• Synthesis and biotinylation of oligosaccharide fragments of mannosylated and 5-deoxy-5-methylthio-xylofuranosylated lipoarabinomannan from Mycobacterium tuberculosis
  作者：Pintu Kumar Mandal、Pratik Rajesh Chheda

  DOI：10.1016/j.carres.2015.01.003

  日期：2015.4

  The attachment of biotin to a molecule provides a powerful tool in biology. Here, we report an efficient synthesis and biotinylation of mannosylated and 5-deoxy-5-methylthio-xylofuranosylated Lipoarabinomannan from Mycobacterium tuberculosis. Preparation of the oligosaccharides involved the sequential addition of thioglycoside donors with arabinofuranosyl-containing acceptors. Methylthio group was introduced near the end of the synthesis. (C) 2015 Elsevier Ltd. All rights reserved.