Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester | 175355-37-0

• 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-5-hydroxy-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester
• 英文别名: [(2S,3S,4S,5R,6R)-5-hydroxy-2-pent-4-enoxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl] 2-chloroacetate
• CAS: 175355-37-0
• 化学式: C₂₇H₃₃ClO₇
• 分子量: 505.008
• InChiKey: DMLIAEKKXAIDPT-OSXMURCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester 在 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 、 silver trifluoromethanesulfonate 、 碳酸氢钠 、 硫脲 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 10.05h， 生成 [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5S,6S)-6-(4,5-dibromopentoxy)-5-[(2R,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate
  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：

  Chloro-acetic acid (4aR,6S,7S,8S,8aR)-8-benzyloxy-6-pent-4-enyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以845 %的产率得到Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-pent-4-enyloxy-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

文献信息

• <i>n</i>-Pentenyl Glycoside Methodology in the Stereoselective Construction of the Tetrasaccharyl Cap Portion of <i>Leishmania</i> Lipophosphoglycan
  作者：Ashok Arasappan、Bert Fraser-Reid

  DOI：10.1021/jo9520102

  日期：1996.1.1

  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.