N-Benzyl-N-{(S)-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-furan-2-yl-methyl}-hydroxylamine | 167640-61-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-Benzyl-N-{(S)-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-furan-2-yl-methyl}-hydroxylamine
• 英文别名: N-benzyl-N-[(S)-[(4S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-(furan-2-yl)methyl]hydroxylamine
• CAS: 167640-61-1
• 化学式: C₂₄H₃₇NO₅Si
• 分子量: 447.647
• InChiKey: WCCSRBHAOVAYFH-BHDDXSALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  64.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-Benzyl-N-{(S)-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-furan-2-yl-methyl}-hydroxylamine 在 水 、 silica gel 、 三氯化钛 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 28.33h， 生成 (1S)-1-(tert-butoxycarbonylamino)-1-deoxy-1-(2-furyl)-2,3-O-isopropylidene-L-threitol
  参考文献：
  名称：

  Addition of 2-Lithiofuran to Chiral α-Alkoxy Nitrones; a Stereoselective Approach to α-Epimeric β-Alkoxy-α-amino Acids

  摘要：

  将 2-锂硫呋喃 (1) 添加到衍生自手性 α-烷氧基醛的 N-苄基硝酮 2a-d 中，以良好的产率和顺式选择性提供 β-烷氧基-α-羟基氨基-2-烷基呋喃。相反，与与二乙基氯化铝预络合的相同硝酮的反应产生相同的加合物，但具有反选择性。三对差向异构羟胺用氯化钛(III) 进行还原性N-脱羟基，然后用四氧化钌进行呋喃基-羧酸转化，得到相应的α-差向异构β-烷氧基-α-氨基酸。

  DOI：

  10.1055/s-1994-25712
• 作为产物：
  描述：

  呋喃-2-基-锂 、 (Z)-N-[4-O-(tert-butyldimethylsilyl)-1-deoxy-2,3-O-isopropylidene-L-threo-1-yliden]benzylamine N-oxide 以 四氢呋喃 为溶剂， 反应 2.0h， 以68%的产率得到N-Benzyl-N-{(S)-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-furan-2-yl-methyl}-hydroxylamine
  参考文献：
  名称：

  Applications of Sugar Nitrones in Synthesis:  The Total Synthesis of (+)-Polyoxin J¹

  摘要：

  A convergent synthesis of the peptidyl nucleoside antibiotic (inhibitor of chitin biosynthesis) polyoxin J (2) by coupling of 5-O-carbamoyl polyoxamic acid (3) and thymine polyoxin C (4) is described. These compounds were prepared by chain elongation and amination of sugar-derived aldehydes employing their nitrones as iminium derivatives and the furan ring as a masked carboxyl. Thus, the stereoselective addition of 2-lithiofuran to the L-threose derived N-benzyl nitrone 5 followed by reduction of the resulting hydroxylamine to amine, carbamoylation of the free hydroxy group, and oxidative cleavage of the furan ring to the carboxylate group gave a protected derivative of 3 (30%). The same method was followed for the synthesis of the ribofuranosyl alpha-amino acid nucleoside 4 (12.6%) starting from the D-ribose derived nitrone 6. The final coupling was performed by the N-hydroxysuccinimide active ester method in DMSO with the Hunig base (i-Pr2EtNH) using a derivative of 3 and unprotected 4.

  DOI：

  10.1021/jo9702913