methyl 6-azido-6-deoxy-3,4-O-isopropylidene-β-D-galactopyranoside | 1144046-98-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl 6-azido-6-deoxy-3,4-O-isopropylidene-β-D-galactopyranoside
• 英文别名: (3aS,4R,6R,7R,7aR)-4-(azidomethyl)-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 1144046-98-9
• 化学式: C₁₀H₁₇N₃O₅
• 分子量: 259.262
• InChiKey: IEZBYZIMIFTZET-SYHAXYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 6-azido-6-deoxy-3,4-O-isopropylidene-β-D-galactopyranoside 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以81%的产率得到methyl 6-amino-6-deoxy-3,4-O-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of glycose carbamides and evaluation of the induction of erythroid differentiation of human erythroleukemic K562 cells

  摘要：

  A series of carbamides derived from 1,2:5,6-di-O-isopropylidene-D-gluco- (1) and D-allofuranose (3) as well as their 5,6-O-deprotected analogues (2 and 4) and methyl 3,4-O-isopropylidene-alpha- and beta-D-galactopyranosides (5 and 6) have been prepared in order to evaluate their ability to induce erythroid differentiation of human erythroleukemic K562 cells. Twenty out of 51 carbamides tested exhibit an appreciable activity as inducers of erythroid differentiation and have been fully characterized and described. (c) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.05.001
• 作为产物：
  描述：

  methyl 3,4-O-isopropylidene-6-O-tosyl-β-D-galactopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 6-azido-6-deoxy-3,4-O-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  A sugar aminoacid for the development of multivalent ligands for Escherichia coli 0157 verotoxin

  摘要：

  Functionalised carbohydrates for incorporation into multivalent ligands for the Escherichia coli O157 verotoxin are highly desirable. Here, we report the synthesis of a sugar aminoacid based on the known Gal-alpha-1,4-Gal ligand for verotoxin in eight steps and in similar to 10% overall yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.021

文献信息

• A sugar aminoacid for the development of multivalent ligands for Escherichia coli 0157 verotoxin
  作者：Darren Gibson、Steven W. Homans、Robert A. Field

  DOI：10.1016/j.tetasy.2009.02.021

  日期：2009.5

  Functionalised carbohydrates for incorporation into multivalent ligands for the Escherichia coli O157 verotoxin are highly desirable. Here, we report the synthesis of a sugar aminoacid based on the known Gal-alpha-1,4-Gal ligand for verotoxin in eight steps and in similar to 10% overall yield. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of glycose carbamides and evaluation of the induction of erythroid differentiation of human erythroleukemic K562 cells
  作者：Martina Landi、Giorgio Catelani、Felicia D'Andrea、Eleonora Ghidini、Gabriele Amari、Puccini Paola、Nicoletta Bianchi、Roberto Gambari

  DOI：10.1016/j.ejmech.2008.05.001

  日期：2009.2

  A series of carbamides derived from 1,2:5,6-di-O-isopropylidene-D-gluco- (1) and D-allofuranose (3) as well as their 5,6-O-deprotected analogues (2 and 4) and methyl 3,4-O-isopropylidene-alpha- and beta-D-galactopyranosides (5 and 6) have been prepared in order to evaluate their ability to induce erythroid differentiation of human erythroleukemic K562 cells. Twenty out of 51 carbamides tested exhibit an appreciable activity as inducers of erythroid differentiation and have been fully characterized and described. (c) 2008 Elsevier Masson SAS. All rights reserved.