(3S,4R,5R,6R)-5-((2R,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-piperidine-3,4-diol | 330998-78-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R,5R,6R)-5-((2R,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-piperidine-3,4-diol
• 英文别名: (3S,4R,5R,6R)-5-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-(phenylmethoxymethyl)piperidine-3,4-diol
• CAS: 330998-78-2
• 化学式: C₃₃H₄₁NO₉
• 分子量: 595.69
• InChiKey: HCOIEGGDDIDBJG-JZXDVHICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  139
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R,6R)-5-((2R,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-piperidine-3,4-diol 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 生成 4-O-β-D-galactopyranosyl-(1->4)-1,5-dideoxy-1,5-imino-D-glucitol
  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：

  (S)-3-Benzyloxy-1-((2S,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-4,5-diisopropoxy-tetrahydro-pyran-2-yloxy)-1-((4R,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-2-one 在 ammonium acetate 、 水 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 2.33h， 生成 (3S,4R,5R,6R)-5-((2R,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-piperidine-3,4-diol
  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

文献信息

• Concise synthesis of 1-deoxy-4- O -β- d -galactopyranosyl- d -nojirimycin avoiding a glycosylation step
  作者：Felicia D'Andrea、Giorgio Catelani、Manuela Mariani、Barbara Vecchi

  DOI：10.1016/s0040-4039(00)02165-1

  日期：2001.2

  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.