2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 229954-87-4

• 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)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-[(2R,3S,4R,5R,6R)-5-(1,3-dioxoisoindol-2-yl)-3-hydroxy-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 229954-87-4
• 化学式: C₄₅H₅₅NO₁₅Si
• 分子量: 878.015
• InChiKey: YRGRSINOTOOZKX-GRCWWAHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  62
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  192
• 氢给体数：
  1
• 氢受体数：
  15

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)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate
  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 在 盐酸 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 、 4 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-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

文献信息

• A High Yielding Chemical Synthesis of Sialyl Lewis x Tetrasaccharide and Lewis x Trisaccharide; Examples of Regio- and Stereodifferentiated Glycosylations
  作者：Ulf Ellervik、Göran Magnusson

  DOI：10.1021/jo981203x

  日期：1998.12.1

  Virtually complete regioselective galactosylation of the diol acceptor p-methoxyphenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-beta-n-glucopyranoside (8) with the donor phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-beta-D-galactopyranoside (11) gave the lactosamine derivative 14, which was fucosylated with the donor 15 to give the Le(x) trisaccharide glycoside 2 after deprotection. Regioselective sialylation of the partially protected Le(x) trisaccharide triol 24 with the sialyl donor 25 gave, after deprotection, the SLe(x) tetrasaccharide glycoside 1. The overall yields of 2 and 1 from the monosaccharide starting materials 8, 11, 15, and 25 were 56% and 29%, respectively. In contrast to the virtually complete regio- and stereoselective galactosylation of 8, fucosylation with the benzyl-protected donor 15 gave the corresponding 1-->3- and 1-->4-linked disaccharides in a ratio of 3.6:1 (highly stereo- but not regioselective glycosylation), whereas fucosylation with acetyl-protected donor 18 gave a 2.2:1 beta/alpha-mixture of 4-O-linked disaccharides (highly regio- but not stereoselective glycosylation).