tert-butyl N-[(2R,3R,4R,5S)-3,4,5-tris(methoxymethoxy)-1-trityloxyhept-6-en-2-yl]carbamate | 205579-02-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: tert-butyl N-[(2R,3R,4R,5S)-3,4,5-tris(methoxymethoxy)-1-trityloxyhept-6-en-2-yl]carbamate
• CAS: 205579-02-8
• 化学式: C₃₇H₄₉NO₉
• 分子量: 651.797
• InChiKey: SZOWNEGDCSYLKK-KMKAFXEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  47
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2R,3R,4R,5S)-3,4,5-tris(methoxymethoxy)-1-trityloxyhept-6-en-2-yl]carbamate 在 sodium tetrahydroborate 、 potassium tert-butylate 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 (2R,3R,4R,5S)-3,4,5-Tris-methoxymethoxy-2-trityloxymethyl-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Improved Synthesis of 1-Deoxynojirimycin and Facile Synthesis of Its Stereoisomers from (S)-Pyroglutamic Acid Derivative

  摘要：

  Improved synthesis of 1-deoxynojirimycin (9) from (E)-alpha,beta-unsaturated ester(1) and facile synthesis of 1-deoxyazasugars (14 and 15) from 10 where both substrates (1 and 10) prepared from (S)-pyroglutamic acid were described.

  DOI：

  10.3987/com-97-s11
• 作为产物：
  描述：

  tert-butyl N-[(2R,3R,4R)-5-hydroxy-3,4-bis(methoxymethoxy)-1-trityloxypentan-2-yl]carbamate 在 copper bromide*dimethyl sulfide 、 N,N-二乙基苯胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 tert-butyl N-[(2R,3R,4R,5S)-3,4,5-tris(methoxymethoxy)-1-trityloxyhept-6-en-2-yl]carbamate
  参考文献：
  名称：

  Improved Synthesis of 1-Deoxynojirimycin and Facile Synthesis of Its Stereoisomers from (S)-Pyroglutamic Acid Derivative

  摘要：

  Improved synthesis of 1-deoxynojirimycin (9) from (E)-alpha,beta-unsaturated ester(1) and facile synthesis of 1-deoxyazasugars (14 and 15) from 10 where both substrates (1 and 10) prepared from (S)-pyroglutamic acid were described.

  DOI：

  10.3987/com-97-s11

文献信息

• Improved Synthesis of 1-Deoxynojirimycin and Facile Synthesis of Its Stereoisomers from (S)-Pyroglutamic Acid Derivative
  作者：Nobuo Ikota、Jun-ichi Hirano、Ranjith Gamage、Hidehiko Nakagawa、Hiroko Hama-Inaba

  DOI：10.3987/com-97-s11

  日期：——

  Improved synthesis of 1-deoxynojirimycin (9) from (E)-alpha,beta-unsaturated ester(1) and facile synthesis of 1-deoxyazasugars (14 and 15) from 10 where both substrates (1 and 10) prepared from (S)-pyroglutamic acid were described.