tert-butyl (3S,4R,5S)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate | 906652-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (3S,4R,5S)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate
• 英文别名: tert-butyl N-[(3S,4R,5S)-4,5-dihydroxy-1-[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]nonadecan-3-yl]carbamate
• CAS: 906652-17-3
• 化学式: C₅₈H₈₃NO₉
• 分子量: 938.298
• InChiKey: IIJIWMCNSORGKE-ZTCILKMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  68
• 可旋转键数：
  34
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S,4R,5S)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 为溶剂， 反应 0.83h， 生成 Hexacosanoic acid {(1S,2R,3S)-2,3-dihydroxy-1-[2-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-heptadecyl}-amide
  参考文献：
  名称：

  Expedient Synthesis of the α-C-Glycoside Analogue of the Immunostimulant Galactosylceramide (KRN7000)

  摘要：

  Key reactions in a concise synthesis of an alpha-C-galactosylceramide analogue of KRN7000 include a diastereoselective alkenylalane addition to an N-tert-butanesulfinyl imine and the use of an epoxidation/carbamate ring opening sequence to install the aminodiol stereotriad.

  DOI：

  10.1021/ol0613057
• 作为产物：
  描述：

  1-十六炔 在 4-二甲氨基吡啶 、 disodium hydrogenphosphate 、 正丁基锂 、 urea-hydrogen peroxide 、 zirconocene hydrochloride 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 21.08h， 生成 tert-butyl (3S,4R,5S)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate
  参考文献：
  名称：

  Expedient Synthesis of the α-C-Glycoside Analogue of the Immunostimulant Galactosylceramide (KRN7000)

  摘要：

  Key reactions in a concise synthesis of an alpha-C-galactosylceramide analogue of KRN7000 include a diastereoselective alkenylalane addition to an N-tert-butanesulfinyl imine and the use of an epoxidation/carbamate ring opening sequence to install the aminodiol stereotriad.

  DOI：

  10.1021/ol0613057

文献信息

• [EN] NOVEL TH2 POLARIZING COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS DE POLARISATION TH2
  申请人：THURGAUISCHE STIFTUNG FUER WISSENSCHAFT UND FORSCHUNG

  公开号：WO2013007792A1

  公开（公告）日：2013-01-17

  The present invention relates to a pharmaceutical composition, particularly to a pharmaceutical composition for use in the treatment and/or prevention of immune-mediated diseases which are characterized by a Th1 environment such as autoimmune diseases, wherein said pharmaceutical composition comprises a compound of formula (I) as defined herein. The present invention also relates to the use of a compound according to formula (I) as defined herein for activating the production of at least one Th2 polarizing cytokine in NKT cells.

  本发明涉及一种药物组合物，特别是用于治疗和/或预防免疫介导疾病的药物组合物，该疾病以Th1环境为特征，如自身免疫疾病，其中所述药物组合物包括本文所定义的化合物(I)。本发明还涉及根据本文所定义的化合物(I)的使用，用于激活NKT细胞中至少一种Th2极化细胞因子的产生。
• Expedient Synthesis of the α-<i>C</i>-Glycoside Analogue of the Immunostimulant Galactosylceramide (KRN7000)
  作者：Peter Wipf、Joshua G. Pierce

  DOI：10.1021/ol0613057

  日期：2006.7.1

  Key reactions in a concise synthesis of an alpha-C-galactosylceramide analogue of KRN7000 include a diastereoselective alkenylalane addition to an N-tert-butanesulfinyl imine and the use of an epoxidation/carbamate ring opening sequence to install the aminodiol stereotriad.