2-(trimethylsilyl)ethyl 2-O-benzoyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 503830-12-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2-O-benzoyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: [(2R,4aR,6S,7S,8S,8aS)-6-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzoate
• CAS: 503830-12-4
• 化学式: C₅₂H₆₀O₁₂Si
• 分子量: 905.127
• InChiKey: ZOKMHYDECRBUID-VQBRZIIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.26
• 重原子数：
  65
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2-O-benzoyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 、 silver trifluoromethanesulfonate 、 一水合肼 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 52.0h， 生成 2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-amino-β-D-glucopyranosyl-(1->3)-β-D-mannopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids

  摘要：

  Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar. have quite unique structures containing GlcNAcbeta-(1-->3)-Man and GalNAcbeta-(1-->4)-GlcNAcbeta-(1-->3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1--> 3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1-->1)-Cer and beta-D-GalNAcp-(1-->4)-beta-D-GlcNAcp-(1-->3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1--> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00295-1
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 tetra(tert-butyl)-ammonium fluoride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 33.17h， 生成 2-(trimethylsilyl)ethyl 2-O-benzoyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids

  摘要：

  Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar. have quite unique structures containing GlcNAcbeta-(1-->3)-Man and GalNAcbeta-(1-->4)-GlcNAcbeta-(1-->3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1--> 3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1-->1)-Cer and beta-D-GalNAcp-(1-->4)-beta-D-GlcNAcp-(1-->3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1--> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00295-1

文献信息

• Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids
  作者：Isao Ohtsuka、Noriyasu Hada、Mutsumi Sugita、Tadahiro Takeda

  DOI：10.1016/s0008-6215(02)00295-1

  日期：2002.11

  Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar. have quite unique structures containing GlcNAcbeta-(1-->3)-Man and GalNAcbeta-(1-->4)-GlcNAcbeta-(1-->3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1--> 3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1-->1)-Cer and beta-D-GalNAcp-(1-->4)-beta-D-GlcNAcp-(1-->3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1--> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages. (C) 2002 Elsevier Science Ltd. All rights reserved.