p-methoxybenzyl (2-acetamido-4-O-allyl-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->3)-3,4-di-O-benzyl-α-L-rhamnopyranoside | 1190718-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxybenzyl (2-acetamido-4-O-allyl-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->3)-3,4-di-O-benzyl-α-L-rhamnopyranoside
• 英文别名: Bn(-3)[allyl(-4)][Bn(-6)]ManNAc(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b1-2)[Bn(-3)][Bn(-4)]Rha(a)-O-Mob；N-[(2S,3S,4R,5S,6R)-2-[(2R,3R,4S,5R,6S)-6-[(2R,3R,4R,5S,6S)-2-[(4-methoxyphenyl)methoxy]-6-methyl-4,5-bis(phenylmethoxy)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)-5-prop-2-enoxyoxan-3-yl]acetamide
• CAS: 1190718-83-2
• 化学式: C₈₀H₈₉NO₁₆
• 分子量: 1320.58
• InChiKey: IGXNEWQSJNGSSL-LIGSAAPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  97
• 可旋转键数：
  35
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  (2R,3R,4S,5S,6S)-2-[(4-methoxyphenyl)methoxy]-6-methyl-4,5-bis(phenylmethoxy)oxan-3-ol 、 Bn(-3)[allyl(-4)][Bn(-6)]ManNAc(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-SPh 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以59%的产率得到p-methoxybenzyl (2-acetamido-4-O-allyl-3,6-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-3,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  A new route for the synthesis of Streptococcus pneumoniae 19F and 19A capsular polysaccharide fragments avoiding the β-mannosamine glycosylation step

  摘要：

  The recently described [Attolino, E.; Bonaccorsi, F.: Catelani, G.; D'Andrea, F. Carbohydr. Res. 2008, 343, 2545-2556.] beta-D-MaNAcp-(1 -> 4)-beta-D-Glcp thiophenyl glycosyl donor 3 was used in alpha-glycosylation reactions of OH-2 and OH-3 of the suitably protected p-MeO-benzyl alpha-L-rhamnopyranoside acceptors 7 and 8. Glycosylation of the axial OH-2 of 7 took place in high yield (76%) and with acceptable stereoselectivity (alpha/beta = 3.4) leading to the protected trisaccharide alpha-11, corresponding to the repeating unit of Streptococcus pneumoniae 19F. The same reaction on equatorial OH-3 of acceptor 8 gave the trisaccharide alpha-15, a constituent of the repeating unit of S. pneumoniae 19A, but in lower yield (41%) and without stereoselection (alpha/beta = 1:1.3). Utilizing the introduced orthogonal protection of OH-1 and OH-4 '', the trisaccharide alpha-11 was transformed into a trisaccharide building block suitable for the synthesis of its phosphorylated oligomers. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.04.012

文献信息

• A new route for the synthesis of Streptococcus pneumoniae 19F and 19A capsular polysaccharide fragments avoiding the β-mannosamine glycosylation step
  作者：Filippo Bonaccorsi、Giorgio Catelani、Stefan Oscarson

  DOI：10.1016/j.carres.2009.04.012

  日期：2009.8

  The recently described [Attolino, E.; Bonaccorsi, F.: Catelani, G.; D'Andrea, F. Carbohydr. Res. 2008, 343, 2545-2556.] beta-D-MaNAcp-(1 -> 4)-beta-D-Glcp thiophenyl glycosyl donor 3 was used in alpha-glycosylation reactions of OH-2 and OH-3 of the suitably protected p-MeO-benzyl alpha-L-rhamnopyranoside acceptors 7 and 8. Glycosylation of the axial OH-2 of 7 took place in high yield (76%) and with acceptable stereoselectivity (alpha/beta = 3.4) leading to the protected trisaccharide alpha-11, corresponding to the repeating unit of Streptococcus pneumoniae 19F. The same reaction on equatorial OH-3 of acceptor 8 gave the trisaccharide alpha-15, a constituent of the repeating unit of S. pneumoniae 19A, but in lower yield (41%) and without stereoselection (alpha/beta = 1:1.3). Utilizing the introduced orthogonal protection of OH-1 and OH-4 '', the trisaccharide alpha-11 was transformed into a trisaccharide building block suitable for the synthesis of its phosphorylated oligomers. (C) 2009 Elsevier Ltd. All rights reserved.