4-methoxyphenyl (6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 774591-89-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl (6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: TrocNH(-2d)[Bn(-6)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-Ph(4-OMe)；2,2,2-trichloroethyl N-[(2S,3R,4R,5R,6R)-4,5-dihydroxy-2-[(2R,3R,4S,5R,6S)-6-(4-methoxyphenoxy)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-6-(phenylmethoxymethyl)oxan-3-yl]carbamate
• CAS: 774591-89-8
• 化学式: C₅₀H₅₄Cl₃NO₁₃
• 分子量: 983.337
• InChiKey: AYNXWRBNPQEGRN-SWNHSHCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  67
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  162
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl (6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 、 在 3 A molecular sieve 、 silver trifluoromethanesulfonate 、 一溴化碘 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.5h， 以40%的产率得到
  参考文献：
  名称：

  Interhalogens (ICl/IBr) and AgOTf in Thioglycoside Activation; Synthesis of Bislactam Analogues of Ganglioside GD3

  摘要：

  The novel promoter system IX/AgOTf (X = Cl or Br) has been evaluated in the synthesis of two bislactam analogues of GD3. We have carried out two high-yielding galactosylations in 97% and 98% yield, respectively, using ICl/AgOTf, and four sialylations in 93%, 59%, 40%, and 44% yield, using IBr/AgOTf, The choice of interhalogen (IX) is determined by the donor type used in the glycosylation. We also report some mechanistic investigations leading to further optimization of the IX/AgOTf promoter system.

  DOI：

  10.1021/jo049184g
• 作为产物：
  描述：

  4-methoxyphenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 在 盐酸 、 guanidinium nitrate 、 3 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 、 一氯化碘 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 4-methoxyphenyl (6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Interhalogens (ICl/IBr) and AgOTf in Thioglycoside Activation; Synthesis of Bislactam Analogues of Ganglioside GD3

  摘要：

  The novel promoter system IX/AgOTf (X = Cl or Br) has been evaluated in the synthesis of two bislactam analogues of GD3. We have carried out two high-yielding galactosylations in 97% and 98% yield, respectively, using ICl/AgOTf, and four sialylations in 93%, 59%, 40%, and 44% yield, using IBr/AgOTf, The choice of interhalogen (IX) is determined by the donor type used in the glycosylation. We also report some mechanistic investigations leading to further optimization of the IX/AgOTf promoter system.

  DOI：

  10.1021/jo049184g

文献信息

• Interhalogens (ICl/IBr) and AgOTf in Thioglycoside Activation; Synthesis of Bislactam Analogues of Ganglioside GD3
  作者：Andréas Meijer、Ulf Ellervik

  DOI：10.1021/jo049184g

  日期：2004.9.1

  The novel promoter system IX/AgOTf (X = Cl or Br) has been evaluated in the synthesis of two bislactam analogues of GD3. We have carried out two high-yielding galactosylations in 97% and 98% yield, respectively, using ICl/AgOTf, and four sialylations in 93%, 59%, 40%, and 44% yield, using IBr/AgOTf, The choice of interhalogen (IX) is determined by the donor type used in the glycosylation. We also report some mechanistic investigations leading to further optimization of the IX/AgOTf promoter system.