Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester | 502185-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-[[(2R,3R,4S,5R,6R)-6-pent-4-enoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 502185-83-3
• 化学式: C₅₈H₇₂O₂₃
• 分子量: 1137.2
• InChiKey: ATFZQDHVZNNKFB-SJTNFKHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  81
• 可旋转键数：
  35
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  267
• 氢给体数：
  0
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-6-ethylsulfanyl-2-(hydroxymethyl)oxan-3-yl] benzoate 、 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester 在 iodonium(di-γ-collidine) perchlorate 、 4 A molecular sieve 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 24.0h， 以92%的产率得到Gal2Ac3Ac4Ac6Ac(b1-4)Glc2Ac3Ac6Ac(b1-6)[Bn(-2)][Bn(-3)][Bn(-4)]Glc(a1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Gal(b)-SEt
  参考文献：
  名称：

  Semi-orthogonality of O-pentenyl and S-ethyl glycosides: application for the oligosaccharide synthesis

  摘要：

  Novel semi-orthogonal glycosylation strategy with the use of 0-pentenyl and thioglycosides has been developed. According to this technique both armed and disarmed thioglycosides can be selectively activated with MeOTf in the presence of either armed or disarmed 0-pentenyl glycosides. The applicability of this novel strategy for the synthesis of a trans-cis glycosylation pattern, not accessible via conventional armed-disarmed approach, has been demonstrated for the synthesis of a linear tetrasaccharide derivative. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02235-9
• 作为产物：
  描述：

  lactose octaacetate 在 3 A molecular sieve 、 三氟化硼乙醚 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 为溶剂， 生成 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Semi-orthogonality of O-pentenyl and S-ethyl glycosides: application for the oligosaccharide synthesis

  摘要：

  Novel semi-orthogonal glycosylation strategy with the use of 0-pentenyl and thioglycosides has been developed. According to this technique both armed and disarmed thioglycosides can be selectively activated with MeOTf in the presence of either armed or disarmed 0-pentenyl glycosides. The applicability of this novel strategy for the synthesis of a trans-cis glycosylation pattern, not accessible via conventional armed-disarmed approach, has been demonstrated for the synthesis of a linear tetrasaccharide derivative. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02235-9

文献信息

• On Orthogonal and Selective Activation of Glycosyl Thioimidates and Thioglycosides: Application to Oligosaccharide Assembly
  作者：Sophon Kaeothip、Alexei V. Demchenko

  DOI：10.1021/jo201117s

  日期：2011.9.16

  Discrimination among S-thiazolinyl (STaz), S-benzoxazolyl (SBox), and S-ethyl anomeric leaving groups was achieved by fine-tuning activation conditions. Preferential glycosidation of a certain leaving group is determined neither by the strength of the activating reagent nor by the stability of the leaving group itself; instead, the type of activation plays the key role. The activation conditions established herein were applied to a sequential five-step synthesis of a hexasaccharide using six monosaccharide building blocks equipped with six different leaving groups.