5-O-benzhydryl-2,3-O-isopropylidene-D-ribonolactone | 1021178-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-O-benzhydryl-2,3-O-isopropylidene-D-ribonolactone
• 英文别名: 5-O-benzhydryl-2,3-O-isopropylidene-D-ribono-1,4-lactone；(3aR,6R,6aR)-6-(benzhydryloxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 1021178-09-5
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: SLFINOSQAFJTFF-BHIYHBOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  5-O-benzhydryl-2,3-O-isopropylidene-D-ribonolactone 在 吡啶 、 sodium azide 、 碘 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 26.0h， 生成 (3aR,6R,6aR)-3a-(azidomethyl)-6-(benzhydryloxymethyl)-2,2-dimethyl-6,6a-dihydrofuro[3,4-d][1,3]dioxol-4-one
  参考文献：
  名称：

  C-Branched Iminosugars: α-Glucosidase Inhibition by Enantiomers of isoDMDP, isoDGDP, and isoDAB–l-isoDMDP Compared to Miglitol and Miglustat

  摘要：

  The Ho crossed aldol condensation provides access to a series of carbon branched iminosugars as exemplified by the synthesis of enantiomeric pairs of isoDMDP, isoDGDP, and isoDAB, allowing comparison of their biological activities with three linear isomeric natural products DMDP, DGDP, and DAB and their enantiomers. L-IsoDMDP [(2S,3S,4R)-2,4-bis(hydroxymethyl)pyrrolidine-3,4-diol], prepared in 11 steps in an overall yield of 4596 from D-lyxonolactone, is a potent specific competitive inhibitor of gut disaccharidases [K-i 0.081 mu M for rat intestinal maltase] and is more effective in the suppression of hyperglycaemia in a maltose loading test than miglitol, a drug presently used in the treatment of late onset diabetes. The partial rescue of the defective F508del-CFTR function in CF-KM4 cells by L-isoDMDP is compared with miglustat and isoLAB in an approach to the treatment of cystic fibrosis.

  DOI：

  10.1021/jo4005487
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 、 二苯基重氮甲烷 以 甲苯 为溶剂， 以97%的产率得到5-O-benzhydryl-2,3-O-isopropylidene-D-ribonolactone
  参考文献：
  名称：

  在不存在任何其他试剂的情况下，通过与二苯基重氮甲烷一起加热，可以高效率地保护醇，包括对叔醇和碱敏感的醇（如二苯甲基醚）

  摘要：

  对于许多合成而言，可在不需要任何酸或碱催化的情况下有效地引入保护基且不易于被酸或碱催化的迁移的保护基是重要的优点。当相应的醇与二苯基重氮甲烷在惰性溶剂（如乙腈或甲苯）中加热时，在中性条件下，糖内酯的苄基[二苯基甲基]醚可以高收率形成；这样就可以在没有任何其他试剂的情况下轻松保护对碱敏感的和高度受阻的叔醇。

  DOI：

  10.1016/j.tetlet.2008.02.042

文献信息

• High yield protection of alcohols, including tertiary and base sensitive alcohols, as benzhydryl ethers by heating with diphenyldiazomethane in the absence of any other reagent
  作者：Daniel Best、Sarah F. Jenkinson、Sebastian D. Rule、Rosemary Higham、Thomas B. Mercer、Richard J. Newell、Alexander C. Weymouth-Wilson、George W.J. Fleet、Sigthor Petursson

  DOI：10.1016/j.tetlet.2008.02.042

  日期：2008.3

  can be introduced efficiently without the need for any acid or base catalysis and which is not prone to acid or base catalysed migration is a significant advantage for many syntheses. Benzhydryl [diphenylmethyl] ethers of sugar lactones are formed in high yield under neutral conditions when the corresponding alcohol is heated with diphenyldiazomethane in an inert solvent such as acetonitrile or toluene;

  对于许多合成而言，可在不需要任何酸或碱催化的情况下有效地引入保护基且不易于被酸或碱催化的迁移的保护基是重要的优点。当相应的醇与二苯基重氮甲烷在惰性溶剂（如乙腈或甲苯）中加热时，在中性条件下，糖内酯的苄基[二苯基甲基]醚可以高收率形成；这样就可以在没有任何其他试剂的情况下轻松保护对碱敏感的和高度受阻的叔醇。
• Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-d-lyxitol [a potent competitive inhibitor of α-d-galactosidase] and of 1,4-dideoxy-1,4-imino-l-lyxitol [a weak competitive inhibitor of α-d-galactosidase] inhibit naringinase, an α-l-rhamnosidase competitively
  作者：Thomas B. Mercer、Sarah F. Jenkinson、Barbara Bartholomew、Robert J. Nash、Saori Miyauchi、Atsushi Kato、George W.J. Fleet

  DOI：10.1016/j.tetasy.2009.10.004

  日期：2009.10

  Benzhydryl protection by diphenyldiazomethane of an alcohol in enantiomeric base-sensitive ribonolactones allows short efficient syntheses of 1,4-dideoxy-1,4-imino-D-lyxitol (DIL) and of 1,4-dideoxy-1,4-imino-L-lyxitol (LIL). DIL showed potent [K-i = 0.13 mu M]-and LIL showed weak [K-i = 113 mu M]-competitive inhibition of alpha-D-galactosidase. Both enantiomers N-benzyl-DIL [K-i = 64 mu M] and N-benzyl-LIL [K-i = 13 mu M] were moderate competitive inhibitors of naringinase, an alpha-L-rhamnosidase. (C) 2009 Elsevier Ltd. All rights reserved.
• <i>C</i>-Branched Iminosugars: α-Glucosidase Inhibition by Enantiomers of isoDMDP, isoDGDP, and isoDAB–<scp>l</scp>-isoDMDP Compared to Miglitol and Miglustat
  作者：Sarah F. Jenkinson、Daniel Best、A. Waldo Saville、James Mui、R. Fernando Martínez、Shinpei Nakagawa、Takahito Kunimatsu、Dominic S. Alonzi、Terry D. Butters、Caroline Norez、Frederic Becq、Yves Blériot、Francis X. Wilson、Alexander C. Weymouth-Wilson、Atsushi Kato、George W. J. Fleet

  DOI：10.1021/jo4005487

  日期：2013.8.2

  The Ho crossed aldol condensation provides access to a series of carbon branched iminosugars as exemplified by the synthesis of enantiomeric pairs of isoDMDP, isoDGDP, and isoDAB, allowing comparison of their biological activities with three linear isomeric natural products DMDP, DGDP, and DAB and their enantiomers. L-IsoDMDP [(2S,3S,4R)-2,4-bis(hydroxymethyl)pyrrolidine-3,4-diol], prepared in 11 steps in an overall yield of 4596 from D-lyxonolactone, is a potent specific competitive inhibitor of gut disaccharidases [K-i 0.081 mu M for rat intestinal maltase] and is more effective in the suppression of hyperglycaemia in a maltose loading test than miglitol, a drug presently used in the treatment of late onset diabetes. The partial rescue of the defective F508del-CFTR function in CF-KM4 cells by L-isoDMDP is compared with miglustat and isoLAB in an approach to the treatment of cystic fibrosis.