1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1,3-propanedithio))-D-2'-glucosyl>-3α-methoxy-4α-styryl-2-azetidinone | 132075-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1,3-propanedithio))-D-2'-glucosyl>-3α-methoxy-4α-styryl-2-azetidinone
• 英文别名: (3R,4S)-1-[(R)-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-(1,3-dithian-2-yl)methyl]-3-methoxy-4-[(E)-2-phenylethenyl]azetidin-2-one
• CAS: 132075-32-2
• 化学式: C₂₇H₃₇NO₆S₂
• 分子量: 535.726
• InChiKey: LTAXSVOOLNJEMR-XLAPCXHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.46
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1,3-propanedithio))-D-2'-glucosyl>-3α-methoxy-4α-styryl-2-azetidinone 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以68%的产率得到4β-benzyl-6α-methoxy-3α-propylthio-2-(1,2;3,4-di-O-isopropylidene-1,2,3,4-tetrahydroxybutyl)-1-aza-bicyclo<3.2.0>heptan-7-one
  参考文献：
  名称：

  Anaya, Josefa; Barton, Derek H. R.; Gero, Stephan D., Angewandte Chemie, 1993, vol. 105, # 6, p. 911 - 913

  摘要：

  DOI：
• 作为产物：
  描述：

  2-amino-2-deoxy-3,4;5,6-di-O-isopropylidene-D-glucose propane-1,3-diyldithioacetal 在 三乙胺 作用下， 生成 1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1,3-propanedithio))-D-2'-glucosyl>-3α-methoxy-4α-styryl-2-azetidinone
  参考文献：
  名称：

  Barton, Derek H. R.; Gateau-Olesker, Alice; Anaya-Mateos, Josefa, Journal of the Chemical Society. Perkin transactions I, 1990, # 11, p. 3211 - 3212

  摘要：

  DOI：

文献信息

• d-Glucosamine propanedithioacetal, an efficient chiral auxiliary in β-Lactam chemistry1Dedicated to Professor Sir Derek H. R. Barton.1
  作者：Josefa Anaya、Stephane D Gero、Manuel Grande、José Ignacio M Hernando、Nieves M Laso

  DOI：10.1016/s0968-0896(98)00264-8

  日期：1999.5

  The synthesis of some monocyclic beta-lactams (monobactams) by the Staudinger reaction using D-glucosamine propanedithioacetal as chiral auxiliary is reported. The influence of several radicals at C-3, C-4, and C-1' (sugar moiety) as well as other structural aspects are considered in relation to the antielastase activity. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Different approaches to the asymmetric synthesis of 1,3,6-trisubstituted and 1,2,3,6-tetrasubstituted carbapenems1 from D-glucosamine
  作者：Josefa Anaya、Derek H.R Barton、Stephane D Gero、Manuel Grande、JoséI.M Hernando、Nieves M Laso

  DOI：10.1016/0957-4166(95)00045-q

  日期：1995.2

  Different stereocontrolled syntheses of optically active 1,3,6-trisubstituted and 1,2,3,6-tetrasubstituted carbapenems(1) are reported. D-glucosamine, as chiral auxiliary, trans-cinnamaldehyde and methoxyacetyl chloride were used as starting materials in the Staudinger ketene-imine monobactam formation. Radical cyclization and oxidation reactions led to the desired carbapenems.
• BARTON, DEREK H. R.;GATEAU-OLESKER, ALICE;ANAYA-MATEOS, JOSEFA;CLEOPHAX, +, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N1, C. 3211-3212
  作者：BARTON, DEREK H. R.、GATEAU-OLESKER, ALICE、ANAYA-MATEOS, JOSEFA、CLEOPHAX, +

  DOI：——

  日期：——