Benzyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid | 95580-52-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid
• 英文别名: benzyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(2,6-di-O-benzyl-4-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside；benzyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→3)-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside；GlcNAc3Ac4Ac6Ac(b1-3)[Bn(-2)][Bn(-6)]Gal4Ac(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-Bn；[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-[(2R,3S,4S,5R,6S)-3-acetyloxy-5-phenylmethoxy-2-(phenylmethoxymethyl)-6-[(2R,3R,4S,5R,6R)-4,5,6-tris(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxyoxan-4-yl]oxyoxan-2-yl]methyl acetate
• CAS: 95580-52-2
• 化学式: C₇₀H₇₉NO₂₀
• 分子量: 1254.39
• InChiKey: DMTVJJBHWAPLJG-VQYKQRDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  91
• 可旋转键数：
  34
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  236
• 氢给体数：
  1
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  Benzyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Lactotriaose-containing carbosilane dendrimers: Syntheses and lectin-binding activities

  摘要：

  Carbosilane dendrimers periphery-functionalized with lactotriaose (GlcNAc beta 1-3Gal beta l-4Glc) with valencies of three, four, six, and twelve were prepared for use in a lectin-binding assay. A lactotriaose derivative was prepared from D-glucosamine and D-lactose derivatives. The N-Troc-protected glucosamine glycosyl donor and 3'-O-unprotected lactose glycosyl acceptor were condensed in the presence of silver trifluoromethanesulfonate and methylsulfenyl bromide to provide corresponding trisaccharide with new beta-1-3 linkages in 92% yield. The protection group of the trisaccharide was transformed into an acetyl group. The 4-pentenyl glycoside was prepared from the acetate via glycosyl bromide. The alkene was converted into acetyl sulfide by addition of thioacetic acid under radical conditions. The lactotriaose unit was linked with carbosilane dendrimers to afford acelyl-protected glycodendrimers. De-O-acetylation of the dendrimers was carried out in the presence of sodium methoxide and then aq NaOH to give the desired lactotriaose clusters using a carbosilane dendrimer backbone. Their biological activities toward WGA were evaluated by fluorescence methods. The binding constants of free lactotriaose and trivalent, tetravalent, hexavalent, and dodecavalent glycodendrimers to WGA were determined to be 1.1 x 10(3), 4.4 x 10(4), 5.1 x 10(4), 2.8 x 10(6), and 1.3 x 10(6) M-1, respectively. The hexavalent glycodendrimer showed a 2500-fold larger binding effect than that of free lactotriaose. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.030
• 作为产物：
  描述：

  benzyl O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1->3)-O-(2,6-di-O-benzyl-4-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 吡啶 、 溶剂黄146 、 锌 作用下， 反应 8.0h， 生成 Benzyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid
  参考文献：
  名称：

  Lactotriaose-containing carbosilane dendrimers: Syntheses and lectin-binding activities

  摘要：

  Carbosilane dendrimers periphery-functionalized with lactotriaose (GlcNAc beta 1-3Gal beta l-4Glc) with valencies of three, four, six, and twelve were prepared for use in a lectin-binding assay. A lactotriaose derivative was prepared from D-glucosamine and D-lactose derivatives. The N-Troc-protected glucosamine glycosyl donor and 3'-O-unprotected lactose glycosyl acceptor were condensed in the presence of silver trifluoromethanesulfonate and methylsulfenyl bromide to provide corresponding trisaccharide with new beta-1-3 linkages in 92% yield. The protection group of the trisaccharide was transformed into an acetyl group. The 4-pentenyl glycoside was prepared from the acetate via glycosyl bromide. The alkene was converted into acetyl sulfide by addition of thioacetic acid under radical conditions. The lactotriaose unit was linked with carbosilane dendrimers to afford acelyl-protected glycodendrimers. De-O-acetylation of the dendrimers was carried out in the presence of sodium methoxide and then aq NaOH to give the desired lactotriaose clusters using a carbosilane dendrimer backbone. Their biological activities toward WGA were evaluated by fluorescence methods. The binding constants of free lactotriaose and trivalent, tetravalent, hexavalent, and dodecavalent glycodendrimers to WGA were determined to be 1.1 x 10(3), 4.4 x 10(4), 5.1 x 10(4), 2.8 x 10(6), and 1.3 x 10(6) M-1, respectively. The hexavalent glycodendrimer showed a 2500-fold larger binding effect than that of free lactotriaose. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.030

文献信息

• A Convenient Synthesis of Partially Benzylated Derivative of β-DGlcpNAc-( 1→3)-β-D-Galp-(1→4)-β-D-Glcp-1-OBn as a Versatile Building Block for Sialyl Lewis X Antigens
  作者：Sameh Soliman、Rafik Bassily、Ramadan El-Sokkary、Mina Nashed

  DOI：10.2174/1570178612666150415235934

  日期：2015.6.4

  Synthesis of the trisaccharide, benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-Dglucopyranosyl-(1→3)-2,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-Dglucopyranoside (9), was achieved from building block derivatives of the component mono- and disaccharide units. Initially the benzyl lactoside acceptor 3, which has a free hydroxyl group at position O-3`, was prepared via selective opening

  三糖苄基2-乙酰氨基-3,6-二-O-苄基-2-脱氧-β-D-吡喃葡萄糖基-（1→3）-2,4,6-三-O-苄基-β-D-的合成半乳糖吡喃糖基-（1→4）-2,3,6-三-O-苄基-β-D-吡喃吡喃糖苷（9）是由单糖和二糖单元的结构单元衍生物制得的。最初，通过选择性地打开3'，4'-环原酸酯衍生物2制备在O-3'位置具有游离羟基的苄基乳糖苷受体3。糖胺基供体2-甲基（3,4，将6-三-O-乙酰基-1,2-二脱氧-（α-D-吡喃吡喃）-[2`，1`：4,5] -2-恶唑啉（4）与3偶联，得到三糖苷5依次进行8-脱O-乙酰化（5→6），苄基化（6→7），苄基化（7→8）和还原性打开亚苄基乙缩醛功能得到目标三糖9，
• Paulsen, Hans; Hadamczyk, Doris; Kutschker, Wolfram, Liebigs Annalen der Chemie, 1985, # 1, p. 129 - 141
  作者：Paulsen, Hans、Hadamczyk, Doris、Kutschker, Wolfram、Buensch, Almuth

  DOI：——

  日期：——