(4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine | 914772-36-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
• 英文别名: (4aR,6S,7R,8S,8aS)-6-[(2R,3R,4S,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-2-phenyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 914772-36-4
• 化学式: C₆₀H₆₀O₁₀S
• 分子量: 973.196
• InChiKey: KJNNFKFEQGMWGZ-LCLSDFMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  71
• 可旋转键数：
  21
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 以76%的产率得到phenyl 2,3,6,2',3',6'-hexa-O-benzyl-1-thio-β-lactoside
  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 IR resin (H+) 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
  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.