[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tert-butyl(dimethyl)silyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one | 498539-40-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tert-butyl(dimethyl)silyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one
• 英文别名: (3aR,4R,7S,7aS)-7-[tert-butyl(dimethyl)silyl]oxy-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-1,3-benzodioxol-5-one
• CAS: 498539-40-5
• 化学式: C₂₂H₄₄O₅Si₂
• 分子量: 444.759
• InChiKey: GTPIFVMRMMSDLF-GDAAHCPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tert-butyl(dimethyl)silyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 在 titanium(IV) isopropylate 、 sodium cyanoborohydride 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 methyl 6-{[(1'R,3'S,4'S,5'R,6'S)-3'-{tert-butyl(dimethyl)silyloxy}-6'-({tert-butyl(dimethyl)silyloxy}methyl)-4',5'-O-(1-methylethylidene)-3',4',5'-trihydroxycyclohexyl]amino}-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  具有C6-或C7环的氨基环糖醇的合成和糖苷酶抑制活性

  摘要：

  从衍生自d-甘露糖醇的C 2对称双环氧化物描述了与用于治疗非胰岛素依赖型糖尿病的伏格列波糖和阿卡波糖有关的Carcarbugars和各种氨基环糖醇的合成。该方法涉及两个关键步骤：多米诺骨烷基化-用2-lithio-1,3-二硫代环己烷衍生物进行环化，以及用伯胺进行还原或还原胺化。这些化合物已被评估为几种糖苷酶的抑制剂，这项研究尤其表明，L- ido或d - manno 1-aminocycloheptane-3,4,5,6-tetrol是α-d-葡萄糖苷酶的抑制剂，K i在微摩尔范围。

  DOI：

  10.1016/j.tet.2003.09.049
• 作为产物：
  描述：

  [3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tert-butyl(dimethyl)silyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以77%的产率得到[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tert-butyl(dimethyl)silyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one
  参考文献：
  名称：

  具有C6-或C7环的氨基环糖醇的合成和糖苷酶抑制活性

  摘要：

  从衍生自d-甘露糖醇的C 2对称双环氧化物描述了与用于治疗非胰岛素依赖型糖尿病的伏格列波糖和阿卡波糖有关的Carcarbugars和各种氨基环糖醇的合成。该方法涉及两个关键步骤：多米诺骨烷基化-用2-lithio-1,3-二硫代环己烷衍生物进行环化，以及用伯胺进行还原或还原胺化。这些化合物已被评估为几种糖苷酶的抑制剂，这项研究尤其表明，L- ido或d - manno 1-aminocycloheptane-3,4,5,6-tetrol是α-d-葡萄糖苷酶的抑制剂，K i在微摩尔范围。

  DOI：

  10.1016/j.tet.2003.09.049

文献信息

• New azadisaccharide analogs as potential antidiabetics
  作者：Christine Gravier-Pelletier、William Maton、Yves Le Merrer

  DOI：10.1016/s0040-4039(02)02016-6

  日期：2002.11

  The synthesis of various aminocyclitols displaying a N-substituted (or unsubstituted) polyhydroxycyclohexylamine structure is described. The strategy relies on two key steps: a tandem alkylation-cyclization of a C-2-symmetrical bis-epoxide derived from D-mannitol and a reductive amination with several amines of the resulting polyhydroxycyciohexan one. Reduction of the latter also allows a rapid access to the corresponding carbasugars. (C) 2002 Published by Elsevier Science Ltd.
• Efficient access to azadisaccharide analogues
  作者：Christine Gravier-Pelletier、William Maton、Thomas Lecourt、Yves Le Merrer

  DOI：10.1016/s0040-4039(01)00756-0

  日期：2001.7

  The synthesis of various aminocyclitols as pseudo-azadisaccharide candidates for glycosidase inhibition is described. The strategy involves the reductive amination with several amines of polyhydroxycycloheptanones resulting from a tandem alkylarion-cyclisation of C-2-symmetrical bis-epoxides derived from D-mannitol. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis and glycosidase inhibitory activity of aminocyclitols with a C6- or a C7-ring
  作者：Christine Gravier-Pelletier、William Maton、Thierry Dintinger、Charles Tellier、Yves Le Merrer

  DOI：10.1016/j.tet.2003.09.049

  日期：2003.10

  The synthesis of carbasugars and various aminocyclitols, related to voglibose and acarbose used in the treatment of non-insulino-dependant diabetes, is described from C2-symmetrical bis-epoxides derived from d-mannitol. The methodology involves two key steps: a domino alkylation–cyclization with 2-lithio-1,3-dithiane derivatives, and reduction or reductive amination with a primary amine. These compounds

  从衍生自d-甘露糖醇的C 2对称双环氧化物描述了与用于治疗非胰岛素依赖型糖尿病的伏格列波糖和阿卡波糖有关的Carcarbugars和各种氨基环糖醇的合成。该方法涉及两个关键步骤：多米诺骨烷基化-用2-lithio-1,3-二硫代环己烷衍生物进行环化，以及用伯胺进行还原或还原胺化。这些化合物已被评估为几种糖苷酶的抑制剂，这项研究尤其表明，L- ido或d - manno 1-aminocycloheptane-3,4,5,6-tetrol是α-d-葡萄糖苷酶的抑制剂，K i在微摩尔范围。