(1S,2S,3S,4R,5S,6R)-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl-(1'->4)-3-azido-5,6-O-isopropylidenedioxycyclohexane-1,2-diol | 1197003-14-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2S,3S,4R,5S,6R)-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl-(1'->4)-3-azido-5,6-O-isopropylidenedioxycyclohexane-1,2-diol
• 英文别名: [(2R,3S,4S,5R,6R)-6-[[(3aS,4R,5S,6S,7S,7aR)-5-azido-6,7-dihydroxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-4-yl]oxy]-3,4,5-triacetoxy-tetrahydropyran-2-yl]methyl acetate；[(2R,3S,4S,5R,6R)-6-[[(3aS,4R,5S,6S,7S,7aR)-5-azido-6,7-dihydroxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-4-yl]oxy]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 1197003-14-7
• 化学式: C₂₃H₃₃N₃O₁₄
• 分子量: 575.527
• InChiKey: QDAZOJGMZOHXTB-KKJYWUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  197
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,4R,5S,6R)-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl-(1'->4)-3-azido-5,6-O-isopropylidenedioxycyclohexane-1,2-diol 在 三苯基膦 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Chemoenzymatic synthesis of glycosyl-deoxyinositol derivatives. First example of a fagopyritol β-analogue containing an aminoinositol unit

  摘要：

  The first synthesis of two fagopyritol beta-analogues (beta-D-galactopyranosyl-(1' -> 1)-conduramine F-4 and beta-D-galactopyranosyl-(1' -> 3)-4-aminodeoxy-L-chiro-inositol) has been accomplished by a chemoenzymatic route in satisfactory yields. The key step of the synthesis is the TMSOTf-promoted glycosylation reaction of a deoxyconduritol derivative. The methodology is amenable to scale-up and expandable to the preparation of other pseudofagopyritols. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.011
• 作为产物：
  描述：

  (1R,2S,5R,6R)-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl-(1'->1)-2-azido-5,6-O-isopropylidenedioxycyclohex-3-ene 在 ruthenium trichloride 、 sodium periodate 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 2.0h， 以91%的产率得到(1S,2S,3S,4R,5S,6R)-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl-(1'->4)-3-azido-5,6-O-isopropylidenedioxycyclohexane-1,2-diol
  参考文献：
  名称：

  Chemoenzymatic synthesis of glycosyl-deoxyinositol derivatives. First example of a fagopyritol β-analogue containing an aminoinositol unit

  摘要：

  The first synthesis of two fagopyritol beta-analogues (beta-D-galactopyranosyl-(1' -> 1)-conduramine F-4 and beta-D-galactopyranosyl-(1' -> 3)-4-aminodeoxy-L-chiro-inositol) has been accomplished by a chemoenzymatic route in satisfactory yields. The key step of the synthesis is the TMSOTf-promoted glycosylation reaction of a deoxyconduritol derivative. The methodology is amenable to scale-up and expandable to the preparation of other pseudofagopyritols. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.011