Acetic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-iodo-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester | 441018-00-4

• 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,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-iodo-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)]Glc6Ac(a1-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Glc1I；[(2R,3R,4S,5R,6S)-6-[[(2R,3R,4S,5R,6R)-6-iodo-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 441018-00-4
• 化学式: C₅₆H₅₉IO₁₁
• 分子量: 1034.98
• InChiKey: FNQWDSHVUVIVGC-AOTKYVILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  68
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-iodo-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester 、 methoxycarbonylmethyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-bis[2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1->6)]-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 在 4 A molecular sieve 、 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 苯 为溶剂， 反应 2.5h， 以93%的产率得到methoxycarbonylmethyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-tetrakis[2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1->6)]-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Solution-Phase Hexasaccharide Synthesis Using Glucosyl Iodides

  摘要：

  [GRAPHIC]Oligosaccharides composed of 1,6-glucosyl residues have been prepared from glucosyl iodides. The reactions are highly stereoselective, giving the a-glycosides as the only isolated products in yields ranging from 84% to 94%. Oligomer synthesis can take place in an iterative 1 + 1 + 1 fashion or in a convergent manner where dimer iodides serve as donors for higher order acceptors.

  DOI：

  10.1021/ol025887d
• 作为产物：
  描述：

  甲基 2,3,4,6-O-四苄基-alpha-D-吡喃葡萄糖苷 在 碘代三甲硅烷 、 4 A molecular sieve 、 四丁基碘化铵 、 N,N-二异丙基乙胺 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 溶剂黄146 、 苯 为溶剂， 反应 5.0h， 生成 Acetic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-iodo-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Solution-Phase Hexasaccharide Synthesis Using Glucosyl Iodides

  摘要：

  [GRAPHIC]Oligosaccharides composed of 1,6-glucosyl residues have been prepared from glucosyl iodides. The reactions are highly stereoselective, giving the a-glycosides as the only isolated products in yields ranging from 84% to 94%. Oligomer synthesis can take place in an iterative 1 + 1 + 1 fashion or in a convergent manner where dimer iodides serve as donors for higher order acceptors.

  DOI：

  10.1021/ol025887d

文献信息

• Lam, Son N.; Gervay-Hague, Jacquelyn, Carbohydrate Research, 2002, vol. 337, # 21-23, p. 1952 - 1966
  作者：Lam, Son N.、Gervay-Hague, Jacquelyn

  DOI：——

  日期：——