Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester | 276241-24-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4R,5R,6R)-3,4-diacetyloxy-5-[(4-nitrophenyl)methoxycarbonylamino]-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 276241-24-8
• 化学式: C₂₂H₂₄Cl₃N₃O₁₂
• 分子量: 628.804
• InChiKey: CYJOOGDPQVXGLH-UJWQCDCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  205
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester 在 sodium dithionite 、 mol. siev. 4 A 、 三乙基硅基三氟甲磺酸酯 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 0.42h， 生成 Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-[(4aR,6S,7R,8R,8aR)-7-acetylamino-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-5-amino-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  N - p -Nitrobenzyloxycarbonyl galactosamine imidate as a glycosyl donor for the efficient synthesis of mucin core-2 analogue

  摘要：

  An efficient synthesis of the mucin core-2 analogue la was accomplished using N-p-nitrobenzyloxycarbonyl(PNZ)-protected trichloroacetimidate 4 as a novel glycosyl donor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00107-4
• 作为产物：
  描述：

  D-galactosamine hydrochloride 在 sodium methylate 、 乙酸肼 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester
  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

• Differential Carbohydrate Recognition of Two GlcNAc-6-sulfotransferases with Possible Roles in L-Selectin Ligand Biosynthesis
  作者：Brian N. Cook、Sunil Bhakta、Teresa Biegel、Kendra G. Bowman、Joshua I. Armstrong、Stefan Hemmerich、Carolyn R. Bertozzi

  DOI：10.1021/ja001224k

  日期：2000.9.1

  Two human GlcNAc-6-sulfotransferases, CHST2 and HEC-GlcNAc6ST, have been recently identified as possible contributors to the inflammatory response by virtue of their participation in L-selectin ligand biosynthesis. Selective inhibitors would facilitate their functional elucidation and might provide leads for antiinflammatory therapy. Here we investigate the critical elements of a disaccharide substrate that are required for recognition by CHST2 and HEC-GlcNAc6ST. A panel of disaccharide analogues, bearing modifications to the pyranose rings and aglycon substituents, were synthesized and screened for substrate activity with each enzyme. Both GlcNAc-6-sulfotransferases required the 2-N-acetamido and 4-hydroxyl groups of a terminal GlcNAc residue for conversion to product. Both enzymes tolerated modifications to the reducing terminal pyranose. Key differences in recognition of an amide group in the aglycon substituent were observed, providing the basis for future glycomimetic inhibitor design.