Thexyldimethylsilyl 6-O-benzyl-β-D-galactopyranoside | 246865-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Thexyldimethylsilyl 6-O-benzyl-β-D-galactopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-2-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-6-(phenylmethoxymethyl)oxane-3,4,5-triol
• CAS: 246865-83-8
• 化学式: C₂₁H₃₆O₆Si
• 分子量: 412.599
• InChiKey: WAYAJEVLIGDIDI-CXQPBAHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Thexyldimethylsilyl 6-O-benzyl-β-D-galactopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 120.75h， 生成 O-(Methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-benzyl-β-D-galactopyranose
  参考文献：
  名称：

  Synthesis of the Sialyl Lewis X Epitope Attached to Glycolipids with Different Core Structures and their Selectin-Binding Characteristics in a Dynamic Test System

  摘要：

  Sialyl Lewis X (sLe(X))/selectin-mediated leukocyte rolling along endothelial cells has recently gained wide interest. In this paper the influence of the spacer length of laterally clustered neoglycolipids 1a-d on cell rolling in a dynamic test system is investigated. The required di-O-hexadecyl glycerols with none, and with three, six, or nine ethylene glycol units as spacer groups (compounds 4a-d) could be readily obtained. The synthesis of 1-O-thexyldimethylsilyl-protected sLe(X) 24 was based on sialylation of 2,3,4-O-unprotected galactose derivative 11 with sialyl phosphite 8 as donor; this afforded the desired disaccharide 12, which was transformed into trichloroacetimidate 14 as disaccharide donor. Reaction of 3-O-unprotected glucosamine derivative 18 with fucosyl donor 20 afforded disaccharide 21, which was transformed into the 4-O-unprotected derivative 23. Reaction of 14 with 23 furnished the desired tetrasaccharide 24 in good yield. Transformation of 24 into the trichloroacetimidate 26 as donor, followed by the reaction with 4a-d as acceptor gave, after deprotection, the target molecules 1a-d. For comparison, 4d was also connected with a sialyl residue (-->31) and with an N-acetylglucosamine residue (-->34). Compounds 1c and 1d with a hexaethylene glycol and a nonaethylene glycol spacer, respectively, were much more efficient in mediating selectin-dependent cell rolling in the dynamic test system than compounds 1a and 1b, which had no spacer (1a), or only a triethylene glycol spacer (1b).

  DOI：

  10.1002/(sici)1521-3765(20000103)6:1<111::aid-chem111>3.0.co;2-x
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-O-benzyl-D-galactopyranose 在 咪唑 、 sodium methylate 、 乙酸肼 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 Thexyldimethylsilyl 6-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Syntheses of α-dystroglycan derived sialylated glycosyl amino acids carrying a novel mannosyl serine/threonine linkage

  摘要：

  An efficient access to the Fmoc protected glycosyl amino acids 20a-d which correspond to the unique sequence NeuNAc-alpha-(2,3)-Gal-beta-(1,4)-GlcNAc-beta-(1,2)-Man-alpha-Ser/Thr recently found in laminin-binding protein alpha-dystroglycan, is described. Tetrasaccharide donor 18 was constructed from monosaccharide blocks 2, 3, 8 and 9 and coupled with Ser/Thr derivatives 19a-d. Resultant glycosyl amino acid 20d was completely deprotected into 1a. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01361-1

文献信息

• Synthesis of the Sialyl Lewis X Epitope Attached to Glycolipids with Different Core Structures and their Selectin-Binding Characteristics in a Dynamic Test System
  作者：Christian Gege、Jan Vogel、Gerd Bendas、Ulrich Rothe、Richard R. Schmidt

  DOI：10.1002/(sici)1521-3765(20000103)6:1<111::aid-chem111>3.0.co;2-x

  日期：2000.1.3

  Sialyl Lewis X (sLe(X))/selectin-mediated leukocyte rolling along endothelial cells has recently gained wide interest. In this paper the influence of the spacer length of laterally clustered neoglycolipids 1a-d on cell rolling in a dynamic test system is investigated. The required di-O-hexadecyl glycerols with none, and with three, six, or nine ethylene glycol units as spacer groups (compounds 4a-d) could be readily obtained. The synthesis of 1-O-thexyldimethylsilyl-protected sLe(X) 24 was based on sialylation of 2,3,4-O-unprotected galactose derivative 11 with sialyl phosphite 8 as donor; this afforded the desired disaccharide 12, which was transformed into trichloroacetimidate 14 as disaccharide donor. Reaction of 3-O-unprotected glucosamine derivative 18 with fucosyl donor 20 afforded disaccharide 21, which was transformed into the 4-O-unprotected derivative 23. Reaction of 14 with 23 furnished the desired tetrasaccharide 24 in good yield. Transformation of 24 into the trichloroacetimidate 26 as donor, followed by the reaction with 4a-d as acceptor gave, after deprotection, the target molecules 1a-d. For comparison, 4d was also connected with a sialyl residue (-->31) and with an N-acetylglucosamine residue (-->34). Compounds 1c and 1d with a hexaethylene glycol and a nonaethylene glycol spacer, respectively, were much more efficient in mediating selectin-dependent cell rolling in the dynamic test system than compounds 1a and 1b, which had no spacer (1a), or only a triethylene glycol spacer (1b).
• Syntheses of α-dystroglycan derived sialylated glycosyl amino acids carrying a novel mannosyl serine/threonine linkage
  作者：Joachim Seifert、Tomoya Ogawa、Yukishige Ito

  DOI：10.1016/s0040-4039(99)01361-1

  日期：1999.9

  An efficient access to the Fmoc protected glycosyl amino acids 20a-d which correspond to the unique sequence NeuNAc-alpha-(2,3)-Gal-beta-(1,4)-GlcNAc-beta-(1,2)-Man-alpha-Ser/Thr recently found in laminin-binding protein alpha-dystroglycan, is described. Tetrasaccharide donor 18 was constructed from monosaccharide blocks 2, 3, 8 and 9 and coupled with Ser/Thr derivatives 19a-d. Resultant glycosyl amino acid 20d was completely deprotected into 1a. (C) 1999 Elsevier Science Ltd. All rights reserved.