octyl 3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside | 172077-88-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: Octyl 4-O-(3.4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside；(2R,3R,4R,5S,6R)-5-[[(3aS,4R,6S,7R,7aR)-7-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-6-(hydroxymethyl)-2-octoxyoxane-3,4-diol
• CAS: 172077-88-2
• 化学式: C₂₃H₄₂O₁₁
• 分子量: 494.58
• InChiKey: YWTLVDOSJVZJAX-QCSHCSNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  octyl 3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 在 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 octyl 2,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Observations on chemical and enzymatic approaches to α-2,3-sialylated octyl β-lactoside

  摘要：

  A comparison of chemical and chemo-enzymatic syntheses of alpha-2,3-sialylated octyl lactoside is reported. The chemical approach, starting from lactose and sialic acid, required 14 steps and proceeded in 5% overall yield; poor a-selectivity in the sialylation step necessitated a difficult and low yielding separation of anomers. A chemoenzymatic approach, employing recombinant Trypanosoma cruzi trans-sialidase to effect the key sialylation reaction, required 10 steps and gave a similar overall yield. Whereas the chemo-enzymatic synthesis required only three chromatographic purification steps overall, the chemical synthesis required at least nine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00265-x
• 作为产物：
  描述：

  octyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 sodium 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 62.0h， 生成 octyl 3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Observations on chemical and enzymatic approaches to α-2,3-sialylated octyl β-lactoside

  摘要：

  A comparison of chemical and chemo-enzymatic syntheses of alpha-2,3-sialylated octyl lactoside is reported. The chemical approach, starting from lactose and sialic acid, required 14 steps and proceeded in 5% overall yield; poor a-selectivity in the sialylation step necessitated a difficult and low yielding separation of anomers. A chemoenzymatic approach, employing recombinant Trypanosoma cruzi trans-sialidase to effect the key sialylation reaction, required 10 steps and gave a similar overall yield. Whereas the chemo-enzymatic synthesis required only three chromatographic purification steps overall, the chemical synthesis required at least nine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00265-x

文献信息

• Substituted lactose derivatives
  申请人：Glycomed Incorporated

  公开号：US05591835A1

  公开（公告）日：1997-01-07

  Compounds and methods of making them having the following formula are described which bind to selectin receptors and thus modulate the course of inflammation, cancer and related diseases by modulating cell-cell adhesion events: ##STR1## wherein each R.sup.1 is independently H or lower alkyl (1-4C); R.sup.2 is H, OH or lower alkyl (1-4C), or a lipophilic group such as a higher alkyl group (5-15C), alkylaryl or one or more additional saccharide residues; R.sup.3 is a negatively charged moiety including SO.sub.4.sup.2-, PO.sub.4.sup.2-, or related group; Y is H or lower alkyl (1-4C); and X is H or --CHR.sub.4 (CHOR.sup.1).sub.2 CHR.sup.5 OR.sup.1 wherein R.sup.4 and R.sup.5 are each independently H, lower alkyl (1-4C), or taken together result in a five- or six-membered ring optionally containing a heteroatom selected from the group consisting of O, S, and NR.sup.1 ; the five- or six-membered ring optionally substituted with one substituent selected from the group consisting of R.sup.1, CH.sub.2 OR.sup.1, OR.sup.1, OOCR.sup.1, NR.sup.1.sub.2, NHCOR.sup.1, and SR.sup.1 with the proviso that if X represents a hexose substituent R.sup.3 and R.sup.4, taken together, cannot provide a hexose substituent.

  本文描述了具有以下式子的化合物及其制备方法，该化合物能够与选择素受体结合，从而通过调节细胞间粘附事件来调节炎症、癌症及相关疾病的进程：## STR1 ## 其中每个R.sup.1独立地为H或较低的烷基（1-4C）；R.sup.2为H、OH或较低的烷基（1-4C），或为亲脂性基团，例如较高的烷基基团（5-15C）、烷基芳基或一个或多个额外的糖基残基；R.sup.3为负电荷基团，包括SO.sub.4.sup.2-、PO.sub.4.sup.2-或相关的基团；Y为H或较低的烷基（1-4C）；X为H或--CHR.sub.4（CHOR.sup.1）.sub.2CHR.sup.5OR.sup.1，其中R.sup.4和R.sup.5各自独立地为H、较低的烷基（1-4C），或者一起形成一个五元或六元环，可选地含有从O、S和NR.sup.1的群中选择的杂原子；该五元或六元环可选地被一个选自R.sup.1、CH.sub.2OR.sup.1、OR.sup.1、OOCR.sup.1、NR.sup.1.sub.2、NHCOR.sup.1和SR.sup.1的基团取代，但是如果X代表一个六糖取代物，则R.sup.3和R.sup.4不能一起提供一个六糖取代物。
• US5591835A
  申请人：——

  公开号：US5591835A

  公开（公告）日：1997-01-07
• US5728685A
  申请人：——

  公开号：US5728685A

  公开（公告）日：1998-03-17