methyl 2-acetamido-2-deoxy-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-3,6-di-O-pivaloyl-α-D-glucopyranoside | 891182-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-2-deoxy-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-3,6-di-O-pivaloyl-α-D-glucopyranoside
• CAS: 891182-60-8
• 化学式: C₃₃H₅₁NO₁₇
• 分子量: 733.764
• InChiKey: VLYSGSRFQWRBKJ-BCGXPDTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  51.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  223.82
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-2-deoxy-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-3,6-di-O-pivaloyl-α-D-glucopyranoside 在 ProtA-GP₃ST 、 sodium methylate 、 6-氨基-9-[3-羟基-5-[(羟基-磺基氧基-磷酰)氧基甲基]-4-膦酰氧基-四氢呋喃-2-基]-嘌呤 、 manganese(ll) chloride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 25.0h， 生成 methyl 2-acetamido-2-deoxy-4-O-(3'-O-sulfo-β-D-galactopyranosyl)-α-D-glucopyranoside sodium salt
  参考文献：
  名称：

  In vitro sulfation of N-acetyllactosaminide by soluble recombinant human β-Gal-3′-sulfotransferase

  摘要：

  Membrane-bound beta-Gal-3'-sulfotransferase (GP3ST) was expressed and used for in vitro sulfation of Tamm-Horsfall glycoprotein. Further, the regioselective transfer of sulfate to an N-acetyllactosamine derivative could be realised with soluble chimeric GMT, also in combination with Lac transglycosylation by means of beta-galactosidase. Two alternative straightforward chemical syntheses for the target compound could be elaborated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.006
• 作为产物：
  描述：

  2,3,4,6-O-四乙酰基-1-硫代-β-D-苯基半乳糖苷 、 methyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以72%的产率得到methyl 2-acetamido-2-deoxy-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-3,6-di-O-pivaloyl-α-D-glucopyranoside
  参考文献：
  名称：

  In vitro sulfation of N-acetyllactosaminide by soluble recombinant human β-Gal-3′-sulfotransferase

  摘要：

  Membrane-bound beta-Gal-3'-sulfotransferase (GP3ST) was expressed and used for in vitro sulfation of Tamm-Horsfall glycoprotein. Further, the regioselective transfer of sulfate to an N-acetyllactosamine derivative could be realised with soluble chimeric GMT, also in combination with Lac transglycosylation by means of beta-galactosidase. Two alternative straightforward chemical syntheses for the target compound could be elaborated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.006