acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside | 850883-19-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,5-diacetyloxy-6-(3-acetylsulfanylpropoxy)-4-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 850883-19-1
• 化学式: C₃₁H₄₄O₁₉S
• 分子量: 752.745
• InChiKey: KPTMDCFDPZGXLG-ILBWNHHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  51
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  263
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  bis[(3-bromopropylsilyl)propyl]dimethylsilane 、 acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (2R,3S,4S,5S,6R)-2-[(2S,3S,4S,5R,6R)-2-[3-[3-[bis[3-[3-[(2S,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxypropylsulfanyl]propyl]-[3-[dimethyl-[3-[tris[3-[3-[(2S,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxypropylsulfanyl]propyl]silyl]propyl]silyl]propyl]silyl]propylsulfanyl]propoxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  Synthesis of carbosilane dendrimers having peripheral mannose and mannobiose

  摘要：

  The mannose monosaccharide derivative, acetylthiopropyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (Man), and the mannobiose derivative, acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2,3',4',6'-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (alpha-1,3-Man), were synthesized respectively. These mannose derivatives were introduced into carbosilane dendrimer scaffolds of the zero and first generations. As a result, six carbosilane dendrimers were functionalized by Man and alpha-1,3-Man. Isothermal titration microcalorimetry was done to determine binding assay between mannose moieties of carbosilane dendrimer and concanavalin A. It was found that carbosilane dendrimers bound more efficiently to concanavalin A than free mannose (Me-alpha-Man) and mannobiose (Me-alpha-1,3-' Man). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.090
• 作为产物：
  描述：

  4,6-O-Benzylidene-1,2-O-ethylidene-β-D-mannopyranose 在 偶氮二异丁腈 、 4 A molecular sieve 、 三氟化硼乙醚 、 sodium acetate 、 silver trifluoromethanesulfonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 99.67h， 生成 acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of carbosilane dendrimers having peripheral mannose and mannobiose

  摘要：

  The mannose monosaccharide derivative, acetylthiopropyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (Man), and the mannobiose derivative, acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2,3',4',6'-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (alpha-1,3-Man), were synthesized respectively. These mannose derivatives were introduced into carbosilane dendrimer scaffolds of the zero and first generations. As a result, six carbosilane dendrimers were functionalized by Man and alpha-1,3-Man. Isothermal titration microcalorimetry was done to determine binding assay between mannose moieties of carbosilane dendrimer and concanavalin A. It was found that carbosilane dendrimers bound more efficiently to concanavalin A than free mannose (Me-alpha-Man) and mannobiose (Me-alpha-1,3-' Man). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.090