4β-acetyl-3β-methoxy-1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1-sulfinyl-3-thiopropane))-D-2'-glucosyl>-2-azetidinone | 155198-02-0

• 英文名称: 4β-acetyl-3β-methoxy-1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1-sulfinyl-3-thiopropane))-D-2'-glucosyl>-2-azetidinone
• CAS: 155198-02-0
• 化学式: C₂₁H₃₃NO₈S₂
• 分子量: 491.627
• InChiKey: GRNDZPQUTZVCHA-CGMOMNFTSA-N

物化性质

• 沸点：
  679.4±55.0 °C(predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  100.6
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4β-acetyl-3β-methoxy-1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1-sulfinyl-3-thiopropane))-D-2'-glucosyl>-2-azetidinone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到Acetic acid (2R,3S)-3-methoxy-4-oxo-1-[(R)-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-(1,1,3-trioxo-1λ⁶,3λ⁴-[1,3]dithian-2-yl)-methyl]-azetidin-2-yl ester
  参考文献：
  名称：

  d-Glucosamine propanedithioacetal, an efficient chiral auxiliary in β-Lactam chemistry1Dedicated to Professor Sir Derek H. R. Barton.1

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(98)00264-8
• 作为产物：
  描述：

  D-glucoasamine hydrochloride 在 二甲基硫 、 TEA 、 对甲苯磺酸 、 臭氧 作用下， 以 甲苯 为溶剂， 反应 10.5h， 生成 4β-acetyl-3β-methoxy-1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1-sulfinyl-3-thiopropane))-D-2'-glucosyl>-2-azetidinone
  参考文献：
  名称：

  d-Glucosamine propanedithioacetal, an efficient chiral auxiliary in β-Lactam chemistry1Dedicated to Professor Sir Derek H. R. Barton.1

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(98)00264-8