(S)-1-((2S,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-1-((4R,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-propan-2-one | 330998-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-((2S,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-1-((4R,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-propan-2-one
• CAS: 330998-75-9
• 化学式: C₃₁H₄₂O₁₂
• 分子量: 606.667
• InChiKey: IGYBZVHAQDCYOI-LPPPRRJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  151.6
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (S)-1-((2S,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-1-((4R,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-propan-2-one 在 水 、 三氟乙酸 作用下， 反应 0.33h， 生成 (2R,3R,4S)-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2,3,6-trihydroxy-5-oxohexanal
  参考文献：
  名称：

  Concise synthesis of 1-deoxy-4- O -β- d -galactopyranosyl- d -nojirimycin avoiding a glycosylation step

  摘要：

  2',6'-Di-O-benzyl-2,3:5,6:3',4'-tri-O-isopropylidenelactose dimethyl acetal was used as starting material for the preparation of the until now unknown 4-O-beta -D-galactopyranosyl-D-xylo-hexos-5-ulose derivatives 7-9, through selective C-5 oxidation of its partially deprotected derivatives 4-6. Hydrolysis of 7-9 with aq. CF3COOH led to deprotected 1,5-dicarbonyl disaccharides 11-12, diastereoselectively transformed without purification into 1-deoxy-4-O-beta -D-galactopyranosyl-D-nojirimycin derivatives in about 60% yield, through a double reductive amination reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02165-1
• 作为产物：
  描述：

  4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 在 二正丁基氧化锡 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲苯 、 氯仿 为溶剂， 反应 13.0h， 以88%的产率得到(S)-1-((2S,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-1-((4R,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-propan-2-one
  参考文献：
  名称：

  Concise synthesis of 1-deoxy-4- O -β- d -galactopyranosyl- d -nojirimycin avoiding a glycosylation step

  摘要：

  2',6'-Di-O-benzyl-2,3:5,6:3',4'-tri-O-isopropylidenelactose dimethyl acetal was used as starting material for the preparation of the until now unknown 4-O-beta -D-galactopyranosyl-D-xylo-hexos-5-ulose derivatives 7-9, through selective C-5 oxidation of its partially deprotected derivatives 4-6. Hydrolysis of 7-9 with aq. CF3COOH led to deprotected 1,5-dicarbonyl disaccharides 11-12, diastereoselectively transformed without purification into 1-deoxy-4-O-beta -D-galactopyranosyl-D-nojirimycin derivatives in about 60% yield, through a double reductive amination reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02165-1