methoxycarbonylmethyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside | 503173-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methoxycarbonylmethyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside
• 英文别名: methyl 2-[(2R,3R,4S,5R,6R)-6-[[(2S,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxymethyl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]sulfanylacetate
• CAS: 503173-61-3
• 化学式: C₅₇H₆₂O₁₂S
• 分子量: 971.178
• InChiKey: UDXYGEZSNDSFFL-GXDXCNARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  70
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  155
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl iodide 、 methoxycarbonylmethyl 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 4.0h， 以92%的产率得到methoxycarbonylmethyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-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 甲醇 、 4 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 、 四丁基碘化铵 、 N,N-二异丙基乙胺 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 苯 为溶剂， 反应 4.0h， 生成 methoxycarbonylmethyl 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

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：——
• Solution-Phase Hexasaccharide Synthesis Using Glucosyl Iodides
  作者：Son N. Lam、Jacquelyn Gervay-Hague

  DOI：10.1021/ol025887d

  日期：2002.6.1

  [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.