p-tolyl N-benzyl-N-benzyloxycarbonyl-2-amino-4,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside | 1225180-87-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl N-benzyl-N-benzyloxycarbonyl-2-amino-4,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: benzyl N-benzyl-N-[(2S,3R,4R,5S,6R)-4-hydroxy-2-(4-methylphenyl)sulfanyl-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]carbamate
• CAS: 1225180-87-9
• 化学式: C₄₂H₄₃NO₆S
• 分子量: 689.873
• InChiKey: KIHMLKTUIAMRCZ-LRHJBHCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-氯-1-己醇 、 p-tolyl N-benzyl-N-benzyloxycarbonyl-2-amino-4,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到6-chlorohexyl N-benzyl-N-benzyloxycarbonyl-2-amino-4,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Joined use of oxazolidinone and desymmetric amino protection: a new strategy for protection of glucosamine

  摘要：

  Joined use of N-benzyl oxazolidinone and N-benzyl-N-benzyloxycarbonyl (N-BnCbz) desymmetric amino-protecting function is reported. The new synthetic approach enables the facile preparation of type I and type 2 LacNAc disaccharides in satisfactory yields. One-pot deprotection of N-BnCbz and O-benzyl ether is achieved by hydrogenolysis under mild conditions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.021
• 作为产物：
  描述：

  p-tolyl N-benzyl-2-amino-4,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 、 氯甲酸苄酯 在 碳酸氢钠 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 2.0h， 以82%的产率得到p-tolyl N-benzyl-N-benzyloxycarbonyl-2-amino-4,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Joined use of oxazolidinone and desymmetric amino protection: a new strategy for protection of glucosamine

  摘要：

  Joined use of N-benzyl oxazolidinone and N-benzyl-N-benzyloxycarbonyl (N-BnCbz) desymmetric amino-protecting function is reported. The new synthetic approach enables the facile preparation of type I and type 2 LacNAc disaccharides in satisfactory yields. One-pot deprotection of N-BnCbz and O-benzyl ether is achieved by hydrogenolysis under mild conditions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.021

文献信息

• Joined use of oxazolidinone and desymmetric amino protection: a new strategy for protection of glucosamine
  作者：Shih-Che Lin、Chin-Sheng Chao、Chiu-Ching Chang、Kwok-Kong T. Mong

  DOI：10.1016/j.tetlet.2010.02.021

  日期：2010.4

  Joined use of N-benzyl oxazolidinone and N-benzyl-N-benzyloxycarbonyl (N-BnCbz) desymmetric amino-protecting function is reported. The new synthetic approach enables the facile preparation of type I and type 2 LacNAc disaccharides in satisfactory yields. One-pot deprotection of N-BnCbz and O-benzyl ether is achieved by hydrogenolysis under mild conditions. (C) 2010 Elsevier Ltd. All rights reserved.