(2R,3S,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-undec-10-enyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-ol | 914772-39-7

• 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: (2R,3S,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-undec-10-enyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-ol
• 英文别名: (2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-undec-10-enoxyoxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 914772-39-7
• 化学式: C₆₅H₇₈O₁₁
• 分子量: 1035.33
• InChiKey: WCGUQWZARBRPTC-NMICSLHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  76
• 可旋转键数：
  33
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-undec-10-enyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-ol 、 1-trichloroacetamido-2-deoxy-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-α-D-galactopyranose 3,4,6-triacetate 在 4 A molecular sieve 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以90%的产率得到[(2R,3R,4R,5R,6S)-3,4-diacetyloxy-6-[(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-undec-10-enoxyoxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl acetate
  参考文献：
  名称：

  An efficient glycosylation reaction for the synthesis of asialo GM2 analogues

  摘要：

  We investigated the coupling reaction of glycosyl donors N-trichloroethoxycarbonyl-galactosamine-O-trichloroacetimidate (2a) and N-p-nitrobenzyloxycarbonyl-galactosamine-O-trichloroacetimidate (2b) with the 4'-OH of lactose derivatives (3a-d) to synthesize key intermediates of asialo GM2 analogues, and found that the glycosylation yield with 2a was 90% or more in all investigated cases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.008
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 盐酸 、 IR resin (H+) 、 camphor-10-sulfonic acid 、 氢溴酸 、 sodium methylate 、 sodium hydride 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 (2R,3S,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-undec-10-enyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  An efficient glycosylation reaction for the synthesis of asialo GM2 analogues

  摘要：

  We investigated the coupling reaction of glycosyl donors N-trichloroethoxycarbonyl-galactosamine-O-trichloroacetimidate (2a) and N-p-nitrobenzyloxycarbonyl-galactosamine-O-trichloroacetimidate (2b) with the 4'-OH of lactose derivatives (3a-d) to synthesize key intermediates of asialo GM2 analogues, and found that the glycosylation yield with 2a was 90% or more in all investigated cases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.008

文献信息

• An efficient glycosylation reaction for the synthesis of asialo GM2 analogues
  作者：Bin Sun、Aliaksei V. Pukin、Gerben M. Visser、Han Zuilhof

  DOI：10.1016/j.tetlet.2006.08.008

  日期：2006.10

  We investigated the coupling reaction of glycosyl donors N-trichloroethoxycarbonyl-galactosamine-O-trichloroacetimidate (2a) and N-p-nitrobenzyloxycarbonyl-galactosamine-O-trichloroacetimidate (2b) with the 4'-OH of lactose derivatives (3a-d) to synthesize key intermediates of asialo GM2 analogues, and found that the glycosylation yield with 2a was 90% or more in all investigated cases. (c) 2006 Elsevier Ltd. All rights reserved.