pent-4-enyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside | 175355-41-6

• 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: pent-4-enyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-2-[(2S,3S,4S,5R,6R)-2-pent-4-enoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 175355-41-6
• 化学式: C₆₁H₆₈O₁₂
• 分子量: 993.204
• InChiKey: ALEBGBHDUTUCSI-VHPBYRQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  73
• 可旋转键数：
  29
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  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 、 pent-4-enyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.05h， 以69%的产率得到[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5S,6S)-5-[(2R,3S,4S,5R,6R)-3-[(2R,3S,4S,5R,6R)-3-acetyloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-(4,5-dibromopentoxy)-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：

  Dibromopentanyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 四丁基碘化铵 、 锌 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 17.0h， 以86%的产率得到pent-4-enyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  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

• Optimization of Glycosylation Reactions in a Microreactor
  作者：Karolin Geyer、Peter H. Seeberger

  DOI：10.1002/hlca.200790046

  日期：2007.2

  Glycosylations are notoriously difficult reactions that require extensive optimization regarding the type of anomeric leaving group, solvent, reaction temperature, and reaction time. Described is the use of a silicon-based microreactor to screen reaction conditions and to scale-up synthetic procedures. For the first time, glycosyl phosphates were employed in a microreactor. The optimized reaction conditions

  众所周知，糖基化是困难的反应，需要对异头离去基团的类型，溶剂，反应温度和反应时间进行大量优化。描述了使用基于硅的微反应器来筛选反应条件并扩大合成程序。第一次，将糖基磷酸酯用于微反应器中。优化的反应条件已成功转移到分批过程中。