methyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside | 1076192-88-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside
• CAS: 1076192-88-5
• 化学式: C₄₉H₄₇Cl₂NO₁₀S
• 分子量: 912.885
• InChiKey: PIRWVGKURCQXJV-WBDHMVDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.05
• 重原子数：
  63.0
• 可旋转键数：
  14.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  111.22
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以88%的产率得到methyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-6-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  A new glycosylation method part 3: study of microwave effects at low temperatures to control reaction pathways and reduce byproducts

  摘要：

  The efficiency of microwave irradiation at low temperature for glycosylations is described. Although oligosaccharide synthesis usually requires reactive donors for glycosylations, which have leaving groups on the another positions, i.e., trichloroacetoimidates, halogenates, thioalkyl glycosides, etc., the suitable donors in our microwave supported synthesis of Lewis X oligosaccharide were very stable acetate derivatives. Regarding glycosylation with a fucosyl acetate donor and a glucosamine acceptor, microwave irradiation with simultaneous cooling improved yields. Moreover, further synthesis to Lewis X derivatives was achieved only with microwave irradiation at low temperatures. Without microwave irradiation, we could only obtain byproducts and none of the designed product at any reaction temperature. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.011
• 作为产物：
  描述：

  C₂₂H₁₉Cl₂NO₆S 、 2,3,4-tris-O-(phenylmethyl)-β-L-fucopyranosyl fluoride 在 二氯二茂锆 4 A molecular sieve 、 silver perchlorate 作用下， 以 乙醚 为溶剂， 反应 18.0h， 以73%的产率得到methyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  A new glycosylation method part 3: study of microwave effects at low temperatures to control reaction pathways and reduce byproducts

  摘要：

  The efficiency of microwave irradiation at low temperature for glycosylations is described. Although oligosaccharide synthesis usually requires reactive donors for glycosylations, which have leaving groups on the another positions, i.e., trichloroacetoimidates, halogenates, thioalkyl glycosides, etc., the suitable donors in our microwave supported synthesis of Lewis X oligosaccharide were very stable acetate derivatives. Regarding glycosylation with a fucosyl acetate donor and a glucosamine acceptor, microwave irradiation with simultaneous cooling improved yields. Moreover, further synthesis to Lewis X derivatives was achieved only with microwave irradiation at low temperatures. Without microwave irradiation, we could only obtain byproducts and none of the designed product at any reaction temperature. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.011