8-methoxycarbonyloctyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside | 225382-19-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 8-methoxycarbonyloctyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-dibenzoyloxy-3-[(2S,3R,4S,5S,6R)-3,4-dibenzoyloxy-5-hydroxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-(9-methoxy-9-oxononoxy)oxan-2-yl]methyl benzoate
• CAS: 225382-19-4
• 化学式: C₆₄H₆₆O₁₈
• 分子量: 1123.22
• InChiKey: SXHBQZYBZSDPKI-NOXILEMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  82
• 可旋转键数：
  33
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  224
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran 、 8-methoxycarbonyloctyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 8-methoxycarbonyloctyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->4)-2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Large-scale chemical and chemo-enzymatic synthesis of a spacer-containing Pk-trisaccharide

  摘要：

  The Pk-trisaccharide, linked to a solid carrier, is a potential agent for neutralization of shiga-like toxin in the gastrointestinal tract. Two approaches to the multigram-scale synthesis of a linkable Pk-trisaccharide derivative were therefore investigated. A four-step chemical synthesis yielded 8-methoxycarbonyloctyl beta-lactoside in 75% yield from lactose. Further conversion of this derivative through either multistep organic synthesis or one-step enzymatic galactosylation with UDP-galactose and recombinant alpha-1.4-Lyalactosyltransferase gave the Pk-trisaccharide derivative 8-methoxycarbonyloctyl alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl-(1-->4)-beta-D-glucopyranoside in 25% and 68% overall yields from commercial lactose, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.12.027
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl bromide 在 4-二甲氨基吡啶 、 三氯化铝 、 三乙胺-硼烷 、 camphor-10-sulfonic acid 、 sodium methylate 、 silver trifluoromethanesulfonate 、 三氟乙酸 、 1,1,3,3-四甲基脲 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 8-methoxycarbonyloctyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Large-scale chemical and chemo-enzymatic synthesis of a spacer-containing Pk-trisaccharide

  摘要：

  The Pk-trisaccharide, linked to a solid carrier, is a potential agent for neutralization of shiga-like toxin in the gastrointestinal tract. Two approaches to the multigram-scale synthesis of a linkable Pk-trisaccharide derivative were therefore investigated. A four-step chemical synthesis yielded 8-methoxycarbonyloctyl beta-lactoside in 75% yield from lactose. Further conversion of this derivative through either multistep organic synthesis or one-step enzymatic galactosylation with UDP-galactose and recombinant alpha-1.4-Lyalactosyltransferase gave the Pk-trisaccharide derivative 8-methoxycarbonyloctyl alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl-(1-->4)-beta-D-glucopyranoside in 25% and 68% overall yields from commercial lactose, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.12.027

文献信息

• Large-scale chemical and chemo-enzymatic synthesis of a spacer-containing Pk-trisaccharide
  作者：Vivekanand P Kamath、Robert E Yeske、Jonathan M Gregson、R.Murray Ratcliffe、Ying R Fang、Monica M Palcic

  DOI：10.1016/j.carres.2003.12.027

  日期：2004.4

  The Pk-trisaccharide, linked to a solid carrier, is a potential agent for neutralization of shiga-like toxin in the gastrointestinal tract. Two approaches to the multigram-scale synthesis of a linkable Pk-trisaccharide derivative were therefore investigated. A four-step chemical synthesis yielded 8-methoxycarbonyloctyl beta-lactoside in 75% yield from lactose. Further conversion of this derivative through either multistep organic synthesis or one-step enzymatic galactosylation with UDP-galactose and recombinant alpha-1.4-Lyalactosyltransferase gave the Pk-trisaccharide derivative 8-methoxycarbonyloctyl alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl-(1-->4)-beta-D-glucopyranoside in 25% and 68% overall yields from commercial lactose, respectively. (C) 2004 Elsevier Ltd. All rights reserved.