((2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester | 339317-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester
• 英文别名: TrocNH(-2d)[Bn(-3)]Glc(a)-O-Bn；2,2,2-trichloroethyl N-[(2S,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2,4-bis(phenylmethoxy)oxan-3-yl]carbamate
• CAS: 339317-37-2
• 化学式: C₂₃H₂₆Cl₃NO₇
• 分子量: 534.821
• InChiKey: SSCXJOSIMPNXRZ-ONUIULTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester 在 溶剂黄146 、 锌 作用下， 以95%的产率得到Benzyl-2-amino-3-O-benzyl-2-desoxy-α-D-glucopyranosid
  参考文献：
  名称：

  Lipid A structures containing novel lipid moieties: synthesis and adjuvant properties

  摘要：

  Structurally well-defined immune stimulatory molecules are important components of new generation molecular vaccines. In this paper, the design and synthesis of two lipid A analogues containing an unnatural tri-lipid acyl group are described. In a totally synthetic liposomal vaccine system, these re-designed lipid A analogues demonstrate potent immune stimulatory properties including antigen specific T-cell activation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00362-1
• 作为产物：
  描述：

  2,2,2-三氯乙酰胺苄酯 在 三氟甲磺酸 、 溶剂黄146 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 ((2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester
  参考文献：
  名称：

  Lipid A structures containing novel lipid moieties: synthesis and adjuvant properties

  摘要：

  Structurally well-defined immune stimulatory molecules are important components of new generation molecular vaccines. In this paper, the design and synthesis of two lipid A analogues containing an unnatural tri-lipid acyl group are described. In a totally synthetic liposomal vaccine system, these re-designed lipid A analogues demonstrate potent immune stimulatory properties including antigen specific T-cell activation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00362-1

文献信息

• SYNTHETIC LIPID-A ANALOGS AND USES THEREOF
  申请人：BIOMIRA, INC.

  公开号：EP1232168A2

  公开（公告）日：2002-08-21
• [EN] SYNTHETIC LIPID-A ANALOGS AND USES THEREOF<br/>[FR] ANALOGUES DE LIPIDE-A DE SYNTHESE ET LEUR UTILISATION
  申请人：BIOMIRA INC

  公开号：WO2001036433A2

  公开（公告）日：2001-05-25

  New synthetic Lipid-A analogs based on monosaccharide (1) and disaccharide (2) derivatives were designed and prepared in the present invention. Both structures (1) and (2) incorporate novel lipid structures (3) and (4) that are not found in nature. Also, novel disaccharide Lipid-A structures (2) that incorporate novel contingents of uniform lipids and where R1, R4 and R5 are the same substitution group of structure (III) were synthesized. Liposome formulations containing totally synthetic components such as synthetic Lipid-A and synthetic lipopeptide derived from tumor-associated MUC1 mucin are described along with their therapeutic utility. Comparative test results of immunostimulating properties and toxicity of Lipid-A analogs (1) and (2) are included.
• Lipid A structures containing novel lipid moieties: synthesis and adjuvant properties
  作者：Zi-Hua Jiang、Mimi V Bach、Wladyslaw A Budzynski、Mark J Krantz、R.Rao Koganty、B.Michael Longenecker

  DOI：10.1016/s0960-894x(02)00362-1

  日期：2002.8

  Structurally well-defined immune stimulatory molecules are important components of new generation molecular vaccines. In this paper, the design and synthesis of two lipid A analogues containing an unnatural tri-lipid acyl group are described. In a totally synthetic liposomal vaccine system, these re-designed lipid A analogues demonstrate potent immune stimulatory properties including antigen specific T-cell activation. (C) 2002 Elsevier Science Ltd. All rights reserved.