2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl trichloroacetimidate | 142800-27-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bn(-6)]Gal(b)-O-C(NH)CCl3；[(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 142800-27-9
• 化学式: C₃₆H₃₀Cl₃NO₉
• 分子量: 726.995
• InChiKey: APTWRDHFKJGCBI-BBQPZQQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl trichloroacetimidate 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 <(6-deoxy-2,3,4-tri-O-benzyl-α-L-galactopyranosyl)-(1->3)>-<(6-O-benzyl-β-D-galactopyranosyl)-(1->4)>-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose
  参考文献：
  名称：

  Remarkable regioselectivity in the chemical glycosylation of glycal acceptors: a concise solution to the synthesis of sialyl-Lewis X glycal.

  摘要：

  DOI：

  10.1021/ja00047a077
• 作为产物：
  描述：

  6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 吡啶 、 盐酸 、 氨 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 55.0h， 生成 2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Application of Glycals to the Synthesis of Oligosaccharides: Convergent Total Syntheses of the Lewis X Trisaccharide Sialyl Lewis X Antigenic Determinant and Higher Congeners

  摘要：

  Exploiting the differences in reactivity of the hydroxyl groups of glucal allows for rapid access to the sLe(x) tetrasaccharide glycal. This compound is readily converted to the title compounds by azaglycosylation followed by deprotection. The use of stannyl alkoxides in the glycosylation-rearrangement step allows for the use of minimally protected glycosides as the glycosyl accepters. Employing a galactal epoxide as a glycosyl donor allows for a maximally convergent synthesis of the Le(x) glycal.

  DOI：

  10.1021/ja00112a007

文献信息

• Remarkable regioselectivity in the chemical glycosylation of glycal acceptors: a concise solution to the synthesis of sialyl-Lewis X glycal.
  作者：Samuel J. Danishefsky、Jacquelyn Gervay、John M. Peterson、Frank E. McDonald、Koshi Koseki、Takeshi Oriyama、David A. Griffith、Chi Huey Wong、David P. Dumas

  DOI：10.1021/ja00047a077

  日期：1992.10
• Application of Glycals to the Synthesis of Oligosaccharides: Convergent Total Syntheses of the Lewis X Trisaccharide Sialyl Lewis X Antigenic Determinant and Higher Congeners
  作者：Samuel J. Danishefsky、Jacquelyn Gervay、John M. Peterson、Frank E. McDonald、Koshi Koseki、David A. Griffith、Takeshi Oriyama、Stephen P. Marsden

  DOI：10.1021/ja00112a007

  日期：1995.2

  Exploiting the differences in reactivity of the hydroxyl groups of glucal allows for rapid access to the sLe(x) tetrasaccharide glycal. This compound is readily converted to the title compounds by azaglycosylation followed by deprotection. The use of stannyl alkoxides in the glycosylation-rearrangement step allows for the use of minimally protected glycosides as the glycosyl accepters. Employing a galactal epoxide as a glycosyl donor allows for a maximally convergent synthesis of the Le(x) glycal.