(4S,6R)-3-tert-butoxycarbonylamino-6-tert-butyldiphenylsilyloxymethyl-4-methoxycarbonyl-tetrahydro-2H-1,3-oxazine | 911225-60-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S,6R)-3-tert-butoxycarbonylamino-6-tert-butyldiphenylsilyloxymethyl-4-methoxycarbonyl-tetrahydro-2H-1,3-oxazine
• 英文别名: 3-O-tert-butyl 4-O-methyl (4S,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-1,3-oxazinane-3,4-dicarboxylate
• CAS: 911225-60-0
• 化学式: C₂₈H₃₉NO₆Si
• 分子量: 513.706
• InChiKey: MYZVBODTGZSMQY-QPPBQGQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,6R)-3-tert-butoxycarbonylamino-6-tert-butyldiphenylsilyloxymethyl-4-methoxycarbonyl-tetrahydro-2H-1,3-oxazine 在 palladium on activated charcoal 吡啶 、 sodium azide 、 氢气 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.25h， 生成 (4S,6R)-6-Aminomethyl-[1,3]oxazinane-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester
  参考文献：
  名称：

  First synthesis of polyoxin M

  摘要：

  Chiral enolate derived from (4R)-4-tert-butyldiphenyisilyloxymethyl-4-butanolide 10 with lithium hexamethyldisilyazide (LiHMDS) was treated with trisyl azide, followed by addition of TMSCI to give (2S,4R)-2-azido-4-[(tei-t-butyldiphenylsilyloxy)methyl]4-butanolide 8 (53%), from which the first total synthesis of polyoxin M (1) was achieved in overall 3.2% yield (13 steps) from D-glutamic acid. Moreover, the synthesis of the reported synthetic intermediate (2S,4R)-4-hydroxyomithine congener 6 for biphenomycins A and B was also achieved in overall 4.1% yield (12 steps) from D-glutamic acid. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.105
• 作为产物：
  描述：

  (2S,4R)-2-amino-4-[(tert-butyldiphenylsilyloxy)methyl]-4-butanolide 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 为溶剂， 反应 25.0h， 生成 (4S,6R)-3-tert-butoxycarbonylamino-6-tert-butyldiphenylsilyloxymethyl-4-methoxycarbonyl-tetrahydro-2H-1,3-oxazine
  参考文献：
  名称：

  First synthesis of polyoxin M

  摘要：

  Chiral enolate derived from (4R)-4-tert-butyldiphenyisilyloxymethyl-4-butanolide 10 with lithium hexamethyldisilyazide (LiHMDS) was treated with trisyl azide, followed by addition of TMSCI to give (2S,4R)-2-azido-4-[(tei-t-butyldiphenylsilyloxy)methyl]4-butanolide 8 (53%), from which the first total synthesis of polyoxin M (1) was achieved in overall 3.2% yield (13 steps) from D-glutamic acid. Moreover, the synthesis of the reported synthetic intermediate (2S,4R)-4-hydroxyomithine congener 6 for biphenomycins A and B was also achieved in overall 4.1% yield (12 steps) from D-glutamic acid. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.105

文献信息

• First synthesis of polyoxin M
  作者：Yuuichi Shiro、Keisuke Kato、Mikio Fujii、Yoshiteru Ida、Hiroyuki Akita

  DOI：10.1016/j.tet.2006.06.105

  日期：2006.9

  Chiral enolate derived from (4R)-4-tert-butyldiphenyisilyloxymethyl-4-butanolide 10 with lithium hexamethyldisilyazide (LiHMDS) was treated with trisyl azide, followed by addition of TMSCI to give (2S,4R)-2-azido-4-[(tei-t-butyldiphenylsilyloxy)methyl]4-butanolide 8 (53%), from which the first total synthesis of polyoxin M (1) was achieved in overall 3.2% yield (13 steps) from D-glutamic acid. Moreover, the synthesis of the reported synthetic intermediate (2S,4R)-4-hydroxyomithine congener 6 for biphenomycins A and B was also achieved in overall 4.1% yield (12 steps) from D-glutamic acid. (c) 2006 Elsevier Ltd. All rights reserved.