6-Bromo-6-deoxy-2,3-O-isopropylidene-D-gulono-1,4-lactone | 142204-16-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Bromo-6-deoxy-2,3-O-isopropylidene-D-gulono-1,4-lactone
• 英文别名: 6-Bromo-6-deoxy-2,3-O-isopropylidene-D-gulono-γ-lactone；6-bromo-6-deoxy-2,3-O-isopropyliden-D-gulono-γ-lactone；(3aR,6S,6aR)-6-[(1S)-2-bromo-1-hydroxyethyl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 142204-16-8
• 化学式: C₉H₁₃BrO₅
• 分子量: 281.103
• InChiKey: BOUSIIIRSJNISB-XZBKPIIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-Bromo-6-deoxy-2,3-O-isopropylidene-D-gulono-1,4-lactone 在 吡啶 、 二丁基氢铝 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 42.0h， 生成 Acetic acid (1R,2S)-2-acetoxy-1-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-bromo-propyl ester
  参考文献：
  名称：

  6-Exo free radical cyclization of acyclic carbohydrate intermediates: a new synthetic route to enantiomerically pure polyhydroxylated cyclohexane derivatives

  摘要：

  The 6-exo free radical cyclization of conveniently functionalized acyclic carbohydrate derivatives is a new and efficient method for the asymmetric synthesis of polyhydroxylated cyclohexane compounds (aminocyclitols, pseudosugars). The scope and versatility of this synthetic route has been analyzed by changing the absolute configuration of the radical precursors and the nature of the radical trap. The yield and stereoselectivity in this process is very structure dependent.

  DOI：

  10.1021/jo00035a017
• 作为产物：
  描述：

  2,3-Isopropylidene-D-gulono-γ-lactone 在 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到6-Bromo-6-deoxy-2,3-O-isopropylidene-D-gulono-1,4-lactone
  参考文献：
  名称：

  脱氧鼠李糖霉素和鼠李糖内酰胺的对映体的合成以及鼠李糖苷酶的抑制作用都没有：δ-内酰胺酶抑制β-甘露糖苷酶

  摘要：

  描述了由D-和L-古洛糖内酯合成脱氧鼠李宁霉素和鼠李糖内酰胺的两种对映体。将对映体脱氧鼠李糖嘧啶和鼠李糖内酰胺作为抑制剂对人肝糖苷酶的作用与脱氧甘露菌素和甘露糖内酰胺进行了比较。这些化合物均未引起对柚皮苷酶（α-L-鼠李糖苷酶）活性的显着抑制。

  DOI：

  10.1016/0040-4020(92)85012-4

文献信息

• Synthesis of, and lack of inhibition of a rhamnosidase by, both enantiomers of deoxyrhamnojirimycin and rhamnolactam: β-mannosidase inhibition by δ-lactams
  作者：Anthony J. Fairbanks、Neil C. Carpenter、George W.J. Fleet、Nigel G. Ramsden、I. Cenci de Bello、Bryan G. Winchester、Samer S. Al-Daher、Gerry Nagahashi

  DOI：10.1016/0040-4020(92)85012-4

  日期：1992.1

  Synthesis of both enantiomers of deoxyrhamnojirimycin and rhamnonolactam from D- and L-gulonolactones are described. The effects as inhibitors of the enantiomeric deoxyrhamnojirimycins and rhamnonolactams on human liver glycosidases are compared with deoxymannojirimycin and mannonolactam. No significant inhibition of the activity of naringinase (an α-L-rhamnosidase) was caused by any of these compounds

  描述了由D-和L-古洛糖内酯合成脱氧鼠李宁霉素和鼠李糖内酰胺的两种对映体。将对映体脱氧鼠李糖嘧啶和鼠李糖内酰胺作为抑制剂对人肝糖苷酶的作用与脱氧甘露菌素和甘露糖内酰胺进行了比较。这些化合物均未引起对柚皮苷酶（α-L-鼠李糖苷酶）活性的显着抑制。
• US5210089A
  申请人：——

  公开号：US5210089A

  公开（公告）日：1993-05-11
• Washiyama, Susumu; Kamiya, Akihiko; Esaki, Sachiko, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 5, p. 847 - 849
  作者：Washiyama, Susumu、Kamiya, Akihiko、Esaki, Sachiko、Tanaka, Ayako、Sugiyama, Naoko、Kamiya, Shintaro

  DOI：——

  日期：——
• 6-Exo free radical cyclization of acyclic carbohydrate intermediates: a new synthetic route to enantiomerically pure polyhydroxylated cyclohexane derivatives
  作者：Jose Marco-Contelles、Carmen Pozuelo、M. L. Jimeno、Luis Martinez、Angeles Martinez-Grau

  DOI：10.1021/jo00035a017

  日期：1992.4

  The 6-exo free radical cyclization of conveniently functionalized acyclic carbohydrate derivatives is a new and efficient method for the asymmetric synthesis of polyhydroxylated cyclohexane compounds (aminocyclitols, pseudosugars). The scope and versatility of this synthetic route has been analyzed by changing the absolute configuration of the radical precursors and the nature of the radical trap. The yield and stereoselectivity in this process is very structure dependent.