6-chlorohexyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->3)-N-benzyl-N-benzyloxycarbonyl-2-amino-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside | 1225180-96-0

• 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: 6-chlorohexyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->3)-N-benzyl-N-benzyloxycarbonyl-2-amino-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• 英文别名: benzyl N-benzyl-N-[(2R,3R,4R,5S,6R)-2-(6-chlorohexoxy)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]carbamate
• CAS: 1225180-96-0
• 化学式: C₆₈H₇₆ClNO₁₁
• 分子量: 1118.8
• InChiKey: OQNYAPQDRTYTRZ-FTMLPLBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  81
• 可旋转键数：
  31
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-chlorohexyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->3)-N-benzyl-N-benzyloxycarbonyl-2-amino-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 、 乙酸酐 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 水 、 溶剂黄146 、 乙酸乙酯 、 吡啶 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 以50%的产率得到6-chlorohexyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-2-acetamido-4,6-di-O-acetyl-2-deoxy-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：

  6-chlorohexyl N-benzyl-N-benzyloxycarbonyl-2-amino-4,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 、 p-methylphenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 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， 反应 0.33h， 以93%的产率得到6-chlorohexyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->3)-N-benzyl-N-benzyloxycarbonyl-2-amino-4,6-di-O-benzyl-2-deoxy-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.