(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-[(2S,3S,4S,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-yloxy]-tetrahydro-pyran-3-ol | 224953-12-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-[(2S,3S,4S,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-yloxy]-tetrahydro-pyran-3-ol
• CAS: 224953-12-2
• 化学式: C₈₁H₉₄O₁₅
• 分子量: 1307.63
• InChiKey: VISJKMXXPGSXDZ-ZMXRXQLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.25
• 重原子数：
  96.0
• 可旋转键数：
  39.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  149.45
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-[(2S,3S,4S,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-yloxy]-tetrahydro-pyran-3-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以93%的产率得到octyl α-D-mannopyranosyl-(1->2)-α-D-mannopyranosyl-(1->5)-β-D-arabinofuranoside
  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：

  octyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->5)-2,3-di-O-benzyl-β-D-arabinofuranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以96%的产率得到(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-[(2S,3S,4S,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-yloxy]-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