allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-6-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 213913-01-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-6-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(1,3-dioxoisoindol-2-yl)-3-hydroxy-6-prop-2-enoxyoxan-4-yl]oxy-4,5-bis[(4-methylbenzoyl)oxy]-2-(4-oxopentanoyloxymethyl)oxan-3-yl] 4-methylbenzoate
• CAS: 213913-01-0
• 化学式: C₅₈H₆₇NO₁₇Si
• 分子量: 1078.25
• InChiKey: WUKYGKZORNMTFG-KTDAZHKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.59
• 重原子数：
  77
• 可旋转键数：
  25
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  226
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-6-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 草酰氯 、 乙酸肼 、 对甲苯磺酸 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 甲胺 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 60.67h， 生成 3-(2-Aminoethylthio)propyl (β-D-glucopyranosyluronic acid)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Preparation of spacer-containing di-, tri-, and tetrasaccharide fragments of the circulating anodic antigen of Schistosoma mansoni for diagnostic purposes

  摘要：

  The chemical synthesis of beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, and beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2 is described. These oligosaccharides represent fragments of the circulating anodic antigen, secreted by the parasite Schistosoma mansoni in the circulatory system of the host. The applied synthesis strategy includes the preparation of a non-oxidised backbone oligosaccharide, with a levulinoyl group at O-6 of the beta-D-glucose residue. After the selective removal of the levulinoyl group, the obtained hydroxyl functions were converted into carboxyl groups, using pyridinium dichromate and acetic anhydride in dichloromethane, to afford the desired glucuronic-acid-containing oligosaccharides. Subsequently, the allyl glycosides have been elongated with cysteamine to give the corresponding aminespacer-containing oligosaccharides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00125-6
• 作为产物：
  描述：

  4-甲氧基苯基Β-D-吡喃葡萄糖苷 在 三乙烯二胺 、 ammonium cerium(IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 2-氯-1-甲基吡啶碘化物 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 甲苯 、 乙腈 为溶剂， 反应 19.0h， 生成 allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-6-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Preparation of spacer-containing di-, tri-, and tetrasaccharide fragments of the circulating anodic antigen of Schistosoma mansoni for diagnostic purposes

  摘要：

  The chemical synthesis of beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, and beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2 is described. These oligosaccharides represent fragments of the circulating anodic antigen, secreted by the parasite Schistosoma mansoni in the circulatory system of the host. The applied synthesis strategy includes the preparation of a non-oxidised backbone oligosaccharide, with a levulinoyl group at O-6 of the beta-D-glucose residue. After the selective removal of the levulinoyl group, the obtained hydroxyl functions were converted into carboxyl groups, using pyridinium dichromate and acetic anhydride in dichloromethane, to afford the desired glucuronic-acid-containing oligosaccharides. Subsequently, the allyl glycosides have been elongated with cysteamine to give the corresponding aminespacer-containing oligosaccharides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00125-6

文献信息

• Synthesis of a tetrasaccharide fragment of the circulating anodic antigen of Schistosoma mansoni
  作者：Koen M. Halkes、Ted M. Slaghek、Henricus J. Vermeer、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/0040-4039(95)01162-b

  日期：1995.8

  A stereocontrolled synthesis of the allyl glycoside of a tetrasaccharide fragment of the O-linked polysaccharide chain of the circulating anodic antigen of Schistosoma mansoni, beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc, is presented.
• Preparation of spacer-containing di-, tri-, and tetrasaccharide fragments of the circulating anodic antigen of Schistosoma mansoni for diagnostic purposes
  作者：Koen M Halkes、Henricus J Vermeer、Ted M Slaghek、Peter A.V van Hooft、Arnoud Loof、Johannis P Kamerling、Johannes F.G Vliegenthart

  DOI：10.1016/s0008-6215(98)00125-6

  日期：1998.5

  The chemical synthesis of beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, and beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2 is described. These oligosaccharides represent fragments of the circulating anodic antigen, secreted by the parasite Schistosoma mansoni in the circulatory system of the host. The applied synthesis strategy includes the preparation of a non-oxidised backbone oligosaccharide, with a levulinoyl group at O-6 of the beta-D-glucose residue. After the selective removal of the levulinoyl group, the obtained hydroxyl functions were converted into carboxyl groups, using pyridinium dichromate and acetic anhydride in dichloromethane, to afford the desired glucuronic-acid-containing oligosaccharides. Subsequently, the allyl glycosides have been elongated with cysteamine to give the corresponding aminespacer-containing oligosaccharides. (C) 1998 Elsevier Science Ltd. All rights reserved.