Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester | 175355-39-2

• 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: Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
• 英文别名: [(2S,3S,4S,5R,6R)-2-(4,5-dibromopentoxy)-4-phenylmethoxy-6-(phenylmethoxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-3-yl] 2-chloroacetate
• CAS: 175355-39-2
• 化学式: C₄₁H₅₁Br₂ClO₁₆
• 分子量: 995.107
• InChiKey: GKNLEIZQQCKVGW-QRAQEZMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  60
• 可旋转键数：
  27
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  187
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 在 碳酸氢钠 、 硫脲 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 以86%的产率得到Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6S)-4-benzyloxy-2-benzyloxymethyl-6-(4,5-dibromo-pentyloxy)-5-hydroxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  n-Pentenyl Glycoside Methodology in the Stereoselective Construction of the Tetrasaccharyl Cap Portion of Leishmania Lipophosphoglycan

  摘要：

  Efficient and high yielding stereoselective assembly of the tetrasaccharyl cap region of the lipophosphoglycan from the protozoan parasite Leishmania using the n-pentenyl glycoside protocol is described in this paper. Both convergent and linear syntheses lead to the protected tetrasaccharide 14; however, the convergent assembly is more efficient in terms of product recovery. Regioselective reductive cleavage of benzylidene acetal 4 with triethylsilane-trifluoroacetic acid system liberates the required C-4 OH in excellent yield, without affecting the resident chloroacetate functionality.

  DOI：

  10.1021/jo9520102
• 作为产物：
  描述：

  pentenyl 4,6-O-benzylidene-α-D-mannopyranoside 在 吡啶 、 三乙基硅烷 、 N-碘代丁二酰亚胺 、 四乙基溴化铵 、 溴 、 三乙基硅基三氟甲磺酸酯 、 二正丁基氧化锡 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.55h， 生成 Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  n-Pentenyl Glycoside Methodology in the Stereoselective Construction of the Tetrasaccharyl Cap Portion of Leishmania Lipophosphoglycan

  摘要：

  Efficient and high yielding stereoselective assembly of the tetrasaccharyl cap region of the lipophosphoglycan from the protozoan parasite Leishmania using the n-pentenyl glycoside protocol is described in this paper. Both convergent and linear syntheses lead to the protected tetrasaccharide 14; however, the convergent assembly is more efficient in terms of product recovery. Regioselective reductive cleavage of benzylidene acetal 4 with triethylsilane-trifluoroacetic acid system liberates the required C-4 OH in excellent yield, without affecting the resident chloroacetate functionality.

  DOI：

  10.1021/jo9520102