methyl 3-O-allyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside | 904301-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-allyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside
• 英文别名: (2R,4aR,6S,7S,8S,8aR)-8-[(2R,3R,4S,5R,6R)-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-4-prop-2-enoxyoxan-2-yl]oxy-6-methoxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 904301-52-6
• 化学式: C₅₁H₅₆O₁₁
• 分子量: 844.999
• InChiKey: LNOLTGVZLLAKNG-NUTMYTLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  62
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 3-O-allyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 在 Wilkinson's catalyst 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 methyl 2,4,6-tri-O-benzyl-(Z)-3-O-prop-1'-enyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 、 methyl 2,4,6-tri-O-benzyl-(E)-3-O-prop-1'-enyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of the Glc3Man N-glycan tetrasaccharide by iterative allyl IAD

  摘要：

  The synthesis of the tetrasaccharide alpha-D-Glcp-(1 -> 2)-alpha-D-Glcp-(1 -> 3)-alpha-D-Glcp-(1 -> 3)-alpha-D-Manp-OMe, corresponding to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved with complete stereocontrol by the use of iterative allyl protecting group mediated intramolecular aglycon delivery (allyl IAD) demonstrating the utility of intramolecular glycosylation for the stereocontrolled construction of multiple glycosidic linkages during the synthesis of an oligosaccharide. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.022
• 作为产物：
  描述：

  1,2,4,6-四-O-乙酰基-3-O-烯丙基-β-D-吡喃葡萄糖 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 三氟化硼乙醚 、 silver trifluoromethanesulfonate 、 sodium 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 43.5h， 生成 methyl 3-O-allyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of the Glc3Man N-glycan tetrasaccharide by iterative allyl IAD

  摘要：

  The synthesis of the tetrasaccharide alpha-D-Glcp-(1 -> 2)-alpha-D-Glcp-(1 -> 3)-alpha-D-Glcp-(1 -> 3)-alpha-D-Manp-OMe, corresponding to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved with complete stereocontrol by the use of iterative allyl protecting group mediated intramolecular aglycon delivery (allyl IAD) demonstrating the utility of intramolecular glycosylation for the stereocontrolled construction of multiple glycosidic linkages during the synthesis of an oligosaccharide. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.022

文献信息

• Synthesis of the Glc3Man N-glycan tetrasaccharide by iterative allyl IAD
  作者：Emanuele Attolino、Ian Cumpstey、Antony J. Fairbanks

  DOI：10.1016/j.carres.2006.02.022

  日期：2006.7

  The synthesis of the tetrasaccharide alpha-D-Glcp-(1 -> 2)-alpha-D-Glcp-(1 -> 3)-alpha-D-Glcp-(1 -> 3)-alpha-D-Manp-OMe, corresponding to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved with complete stereocontrol by the use of iterative allyl protecting group mediated intramolecular aglycon delivery (allyl IAD) demonstrating the utility of intramolecular glycosylation for the stereocontrolled construction of multiple glycosidic linkages during the synthesis of an oligosaccharide. (c) 2006 Elsevier Ltd. All rights reserved.