Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester | 174577-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
• CAS: 174577-00-5
• 化学式: C₂₄H₃₃BrO₁₅
• 分子量: 641.421
• InChiKey: YDKXMSABLBRJKM-RVDCXFAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  185.49
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2,3,6,2',3'-penta-O-benzyl-4',6'-O-benzylidene-α,α-D-trehalose 、 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 在 palladium on activated charcoal 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 生成 O-(6-Deoxy-α-D-glucopyranosyl)-(1->4)-O-β-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl α-D-glucopyranoside
  参考文献：
  名称：

  Selectively deoxygenated sulfated tetrasaccharides as probes for the investigation of smooth muscle cell antiproliferative activity

  摘要：

  DOI：

  10.1016/0960-894x(95)00554-7
• 作为产物：
  描述：

  Allyl 2,3,6,2',3'-Penta-O-acetyl-β-maltoside 在 palladium on activated charcoal 吡啶 、 咪唑 、 氢溴酸 、 氢气 、 碘 、 sodium acetate 、 溶剂黄146 、 三乙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 甲苯 为溶剂， 反应 20.5h， 生成 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Selectively deoxygenated sulfated tetrasaccharides as probes for the investigation of smooth muscle cell antiproliferative activity

  摘要：

  DOI：

  10.1016/0960-894x(95)00554-7

文献信息

• Selectively Deoxygenated Derivatives of β-Maltosyl-(1→4)-Trehalose as Biological Probes
  作者：Hans Peter Wessel、Michel Trumtel、Rudolf Minder

  DOI：10.1080/07328309608005672

  日期：1996.7

  The four derivatives of beta-maltosyl-(1 --> 4)-trehalose have been synthesized, which are monodeoxygenated at the site of one of the primary hydroxyl groups. The tetrasaccharides were constructed in [2+2] block syntheses. Thus, 6'''-deoxy-beta-maltosyl-(1 --> 4)-trehalose was prepared by selective iodination of allyl 2,3,6,2',3'-penta-O-acetyl-beta-maltoside (3) followed by catalytic hydrogenolysis and coupling with 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranosyl 2',3',6'-tri-O-benzyl-alpha-D-glucopyranoside (9), and 6 ''-deoxy-beta-maltosyl-(1 --> 4)-trehalose by selective iodination of allyl 4',6'-O-isopropylidene-beta-maltoside (14), coupling with 9, and one-step hydrogenolysis at the tetrasaccharide level. For the synthesis of 6'-deoxy-beta-maltosyl-(1 --> 4)-trehalose, the diol 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranosyl 2',3'-di-O-benzyl-alpha-D-glucopyranoside (22) was selectively iodinated and glycosylated with acetobromomaltose followed by catalytic hydrogenolysis. The 6-deoxy-beta-maltosyl-(1 --> 4)-trehalose was obtained upon selective iodination of a tetrasaccharide diol.