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 | 227601-42-5

• 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-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)]GlcNAc(b1-3)[Bn(-2)][Bn(-4)][Bn(-6)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-allyl；N-[(2S,3R,4R,5S,6R)-2-[(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-5-hydroxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 227601-42-5
• 化学式: C₇₉H₈₇NO₁₆
• 分子量: 1306.56
• InChiKey: VGRNRHQAHISHMZ-RTVKYORVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  96
• 可旋转键数：
  35
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  179
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  4,6-di-O-acetyl-2-O-benzoyl-3-O--α-D-galactopyranosyl trichloroacetimidate 、 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 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到allyl-O--(1->3)-O-(4,6-di-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-O-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-...
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  allyl-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-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 4 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以80%的产率得到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：

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

  摘要：

  DOI：

文献信息

• Synthesis of 3-O-sulfoglucuronyl lacto-N-neotetraose 2-aminoethyl glycoside and biotinylated neoglycoconjugates thereof
  作者：Andrei V Kornilov、Andrey A Sherman、Leonid O Kononov、Alexander S Shashkov、Nikolay E Nifant'ev

  DOI：10.1016/s0008-6215(00)00258-5

  日期：2000.12

  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.