2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside | 229954-86-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS: 229954-86-3
• 化学式: C₄₅H₅₃NO₁₅Si
• 分子量: 875.999
• InChiKey: BUTNYUOBRDMERX-CQWBZQHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  62.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  180.89
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 吡啶 、 盐酸 、 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Synthesis and NMR assignments of galactosylgloboside and its β-d-GalNAc-(1→4)-α-d-Gal-linked positional isomer in a conjugatable form

  摘要：

  Two pentasaccharides suitable for conjugation, namely 3-aminopropyl glactosylgloboside and its beta-D-GalNAc-(1 -->4)-alpha-D-Gal-linked positional isomer, were synthesized from 3(III),4(III)-di-O-unprotected globotrioside and the trichloroacetimidate of beta-D-Gal-(1 --> 3)-beta-D-GalNPhth derivative. Glycosylation at both positions led to the formation of beta-D-GalNPhth-(1-->4)-alpha-D-Gal and beta-D-GalNPhth-(1-->3)-alpha-D-Gal-linked products in a ratio of 1:1 without selectivity. Complete NMR spectral assignments are also described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00018-x
• 作为产物：
  描述：

  ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-thiogalactopyranoside 、 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and NMR assignments of galactosylgloboside and its β-d-GalNAc-(1→4)-α-d-Gal-linked positional isomer in a conjugatable form

  摘要：

  Two pentasaccharides suitable for conjugation, namely 3-aminopropyl glactosylgloboside and its beta-D-GalNAc-(1 -->4)-alpha-D-Gal-linked positional isomer, were synthesized from 3(III),4(III)-di-O-unprotected globotrioside and the trichloroacetimidate of beta-D-Gal-(1 --> 3)-beta-D-GalNPhth derivative. Glycosylation at both positions led to the formation of beta-D-GalNPhth-(1-->4)-alpha-D-Gal and beta-D-GalNPhth-(1-->3)-alpha-D-Gal-linked products in a ratio of 1:1 without selectivity. Complete NMR spectral assignments are also described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00018-x