1,2-Dideoxy-3,4-O-(1-methylethylidene)-D-threo-pent-1-ynitol | 320396-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-Dideoxy-3,4-O-(1-methylethylidene)-D-threo-pent-1-ynitol
• 英文别名: (2R,3R)-2,3-(O-isopropylidene)pent-4-yn-1-ol；[(4R,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 320396-46-1
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: WVBSRHKZWGFGDO-RNFRBKRXSA-N

物化性质

• 沸点：
  209.7±35.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-Dideoxy-3,4-O-(1-methylethylidene)-D-threo-pent-1-ynitol 在 9-borabicyclo[3.3.1]nonane dimer 、 四溴化碳 、 萘-1,4-二腈 、 四丁基碘化铵 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 、 乙腈 为溶剂， 反应 122.5h， 生成 [(3aR,7R,7aR)-5-Benzyl-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]pyridin-7-yl]methanol
  参考文献：
  名称：

  A Novel Approach to Both the Enantiomers of Potent Glycosidase Inhibitor Isofagomine via PET-Promoted Cyclization of 1-[Benzyl(trimethylsilyl-methyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-threo-pent-4-ynitol

  摘要：

  在合成 1-N-iminosugar 型糖苷酶抑制剂时，利用 PET 生成的δ-三甲基硅甲胺自由基阳离子环化到系链炔基的方法解决了在立体中心旁生成氨基甲基的问题。(+)- 和 (-)-isofagomine 的合成证明了这一方法的成功，isofagomine 是一种极其有效的 1-N-iminosugar 类δ-糖苷酶抑制剂。

  DOI：

  10.1055/s-2001-15063
• 作为产物：
  描述：

  [(4R,5R)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyne 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以85%的产率得到1,2-Dideoxy-3,4-O-(1-methylethylidene)-D-threo-pent-1-ynitol
  参考文献：
  名称：

  A Novel Approach to Both the Enantiomers of Potent Glycosidase Inhibitor Isofagomine via PET-Promoted Cyclization of 1-[Benzyl(trimethylsilyl-methyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-threo-pent-4-ynitol

  摘要：

  在合成 1-N-iminosugar 型糖苷酶抑制剂时，利用 PET 生成的δ-三甲基硅甲胺自由基阳离子环化到系链炔基的方法解决了在立体中心旁生成氨基甲基的问题。(+)- 和 (-)-isofagomine 的合成证明了这一方法的成功，isofagomine 是一种极其有效的 1-N-iminosugar 类δ-糖苷酶抑制剂。

  DOI：

  10.1055/s-2001-15063

文献信息

• Convergent Approach toward the Synthesis of the Stereoisomers of C-6 Homologues of 1-Deoxynojirimycin and Their Analogues:  Evaluation as Specific Glycosidase Inhibitors
  作者：Ganesh Pandey、Shrinivas G. Dumbre、M. Islam Khan、M. Shabab

  DOI：10.1021/jo061455v

  日期：2006.10.1

  A new and stereoselective strategy is developed to synthesize an appropriate template 9 to obtain C-6 homologues of 1-deoxyazasugars such as 1-deoxy-d-galactohomonojirimycin (5), 1-deoxy-4-hydroxymethyl-d-glucohomonojirimycin (6), and their enantiomers. The template 9 is also used to obtain neutral nonbasic pseudo-glyconolactam (8), C-4 amino, and methyl analogues of 1-deoxy-homonojirimycin as new

  一种新的和立体的策略被显影，以合成相应的模板9，得到的C-6同系物1-deoxyazasugars如1-脱氧d -galactohomonojirimycin（5），1-脱氧-4-羟甲基- d -glucohomonojirimycin（6） ，及其对映体。模板9还用于获得中性的非碱性伪乙内酰胺（8），C-4氨基和1-脱氧-homoojirimycin的甲基类似物，作为1-脱氧高纯糖的新类似物。发现化合物5是α-半乳糖苷酶的有效和特异性抑制剂（K i = 1.7μM）。类似的化合物6（Ki = 28μM）， ent - 5（ K i = 129μM）和ent - 6（ K i = 12μM）表现出对β-葡萄糖苷酶的特异性抑制作用。
• A β-lactam-azasugar hybrid as a competitive potent galactosidase inhibitor
  作者：Ganesh Pandey、Shrinivas G. Dumbre、M. Islam Khan、M. Shabab、Vedavati G. Puranik

  DOI：10.1016/j.tetlet.2006.09.005

  日期：2006.11

  A beta-lactam-azasugar hybrid (polyhydroxylated carbacephem) has been designed and synthesized as a potent glycosidase inhibitor. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of exo-methylenedifluorocyclopentanes as precursors of fluorinated carbasugars by 5-exo-dig radical cyclization
  作者：Gaëlle Fourrière、Eric Leclerc、Jean-Charles Quirion、Xavier Pannecoucke

  DOI：10.1016/j.jfluchem.2011.02.015

  日期：2012.2

  The synthesis of polyhydroxylated 1,1-difluoro-5-methylenecyclopentanes is described. The sequence involves an addition of PhSeCF2TMS to a tartrate-derived aldehyde or its corresponding tert-butanesulfinylimines followed by a radical cyclization. The use of a benzyl protected substrate led to an unproductive 1,5-hydrogen transfer after cyclization but the desired compound was eventually obtained from the unprotected substrate. A hydroboration/oxidation sequence was investigated on these 1,1-difluoro-5-methylenecyclopentanes as it would provide fluorinated carbasugars, a new and promising class of glycomimetics. Unfortunately, this reaction was poorly efficient and its regioselectivity not the expected one. (C) 2011 Elsevier B.V. All rights reserved.
• A general strategy towards the synthesis of 1-N-iminosugar type glycosidase inhibitors: demonstration by the synthesis of d- as well as l-glucose type iminosugars (isofagomines)
  作者：Ganesh Pandey、Manmohan Kapur

  DOI：10.1016/s0040-4039(00)01553-7

  日期：2000.11

  Both enantiomers of isofagomine, the potent glycosidase inhibitor of a type 1-N-iminosugar have been synthesized by the intramolecular cyclization of the PET generated alpha -trimethylsilylmethylamine radical cation with the appropriate tethered acetylene moiety. (C) 2000 Published by Elsevier Science Ltd.
• A Novel Approach to Both the Enantiomers of Potent Glycosidase Inhibitor Isofagomine via PET-Promoted Cyclization of 1-[Benzyl(trimethylsilyl-methyl)amino]-1,4,5-trideoxy-2,3-<b><i>O</i></b>-(1-methylethylidene)-<b><i>threo</i></b>-pent-4-ynitol
  作者：Ganesh Pandey、Manmohan Kapur

  DOI：10.1055/s-2001-15063

  日期：——

  The cyclization of PET-generated α-trimethylsilylmethylamine radical cation to a tethered acetylene moiety has been exploited to solve the problem of the generation of an aminomethyl group next to a stereocenter in the synthesis of 1-N-iminosugar type glycosidase inhibitors. Its success is demonstrated by the synthesis of (+)- as well as (-)-isofagomine, an extremely potent β-glucosidase inhibitor of the 1-N-iminosugar class.

  在合成 1-N-iminosugar 型糖苷酶抑制剂时，利用 PET 生成的δ-三甲基硅甲胺自由基阳离子环化到系链炔基的方法解决了在立体中心旁生成氨基甲基的问题。(+)- 和 (-)-isofagomine 的合成证明了这一方法的成功，isofagomine 是一种极其有效的 1-N-iminosugar 类δ-糖苷酶抑制剂。