allyl-O-(2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-O-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 227601-56-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl-O-(2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-O-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: Bn(-3)[Bn(-6)]GlcNAc4Ac(b1-3)[Bn(-2)][Bn(-4)][Bn(-6)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-allyl；[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enoxyoxan-3-yl]oxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 227601-56-1
• 化学式: C₈₁H₈₉NO₁₇
• 分子量: 1348.59
• InChiKey: HOHVKRLPIYCKTI-XLBOZMRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  99
• 可旋转键数：
  37
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  185
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  allyl-O-(2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-O-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 allyl-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-O-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 3-O-sulfoglucuronyl lacto-N-neotetraose 2-aminoethyl glycoside and biotinylated neoglycoconjugates thereof

  摘要：

  The 2-aminoethyl glycoside of pentasaccharide 3-O-sulfo-GlcA(beta -1 --> 3)Gal(beta -1 --> 4)GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta (1) and its conjugates with biotin and biotinylated polyacrylic acid were synthesized as molecular probes to investigate the recognition of the HNK-1 epitope containing carbohydrates by proteins. Key steps in the first of two investigated schemes for the preparation of the target compound 1 were (a) assembling of the pentasaccharide backbone (compound 10) by glycosylation of selectively substituted allyl glycoside of the trisaccharide GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta with glucuronyl-galactose glycosyl donor, (b) transformation of the allyl aglycon in 10 into 2-azidoethyl one (to give 11), (c) selective deprotection of the OH group at C-3 of the GlcA residue in 11 via saponification, intramolecular formation of 6,3-lacton (13) and its methanolysis, and (d) subsequent O-sulfation. The alternative scheme with the use of 2-azido-ethyl glycoside of the trisaccharide GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta instead of the allyl glycoside 6 was less effective due to smaller yield at the step of pentasaccharide synthesis. Additionally to 1 the 2-aminoethyl glycosides of the oligosaccharides GlcA(beta -1 --> 3)Gal(beta -1 --> 4)GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta, 3-O-sulfo-GlcA(beta -1 --> 3)Gal(beta, and GlcA(beta -1 --> 3)Gal(beta were also synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00258-5
• 作为产物：
  描述：

  乙酸酐 、 allyl-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-O-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 吡啶 作用下， 反应 8.0h， 以2.6 mg的产率得到allyl-O-(2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-O-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Kononov; Kornilov; Sherman, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 8, p. 537 - 550

  摘要：

  DOI：