(1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol | 227930-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol
• 英文别名: benzyl (1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)cyclohex-2-enylcarbamate；benzyl N-[(1S,4R,5S,6S)-4,5,6-tris(phenylmethoxy)-3-(phenylmethoxymethyl)cyclohex-2-en-1-yl]carbamate
• CAS: 227930-76-9
• 化学式: C₄₃H₄₃NO₆
• 分子量: 669.818
• InChiKey: QGXDGABZPCIHNP-SOFKUOBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol 在 吡啶 、 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 penta-N,O-acetyl-(+)-valienamine
  参考文献：
  名称：

  Carbasaccharidesvia Ring-Closing Alkene Metathesis. A Synthesis of (+)-Valienamine fromD-Glucose

  摘要：

  DOI：

  10.1002/(sici)1522-2675(19990505)82:5<645::aid-hlca645>3.0.co;2-k
• 作为产物：
  描述：

  3,4,5-tri-O-benzyl-6-C-[(benzyloxy)methyl]-1,2,7,8-tetradeoxy-L-ido-octa-1,7-dienitol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 四溴化碳 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 169.5h， 生成 (1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol
  参考文献：
  名称：

  Carbasaccharidesvia Ring-Closing Alkene Metathesis. A Synthesis of (+)-Valienamine fromD-Glucose

  摘要：

  DOI：

  10.1002/(sici)1522-2675(19990505)82:5<645::aid-hlca645>3.0.co;2-k

文献信息

• Total synthesis of (+)-valienamine and (−)-1-epi-valienamine via a highly diastereoselective allylic amination of cyclic polybenzyl ether using chlorosulfonyl isocyanate
  作者：Qing Ri Li、Seung In Kim、Sook Jin Park、Hye Ran Yang、A Reum Baek、In Su Kim、Young Hoon Jung

  DOI：10.1016/j.tet.2013.09.098

  日期：2013.12

  The total synthesis of (+)-valienamine and (−)-1-epi-valienamine was concisely accomplished from readily available d-glucose via a highly diastereoselective amination of chiral benzylic ether using chlorosulfonyl isocyanate, intramolecular olefin metathesis, and diastereoselective reduction of cyclic enone using l-Selectride as the key steps.

  （+）-戊烯胺和（-）-1-表-戊烯胺的总合成是由易得的d-葡萄糖通过使用氯磺酰基异氰酸酯进行手性苄基醚的高度非对映选择性胺化，分子内烯烃复分解和非对映选择性还原环而完成使用l -Selectride作为关键步骤。
• Pseudoglycosyltransferase Catalyzes Nonglycosidic C–N Coupling in Validamycin A Biosynthesis
  作者：Shumpei Asamizu、Jongtae Yang、Khaled H. Almabruk、Taifo Mahmud

  DOI：10.1021/ja203574u

  日期：2011.8.10

  Glycosyltransferases are ubiquitous in nature. They catalyze a glycosidic bond formation between sugar donors and sugar or nonsugar acceptors to produce oligo/polysaccharides, glycoproteins, glycolipids, glycosylated natural products, and other sugar-containing entities. However, a trehalose 6-phosphate synthase-like protein has been found to catalyze an unprecedented nonglycosidic C-N bond formation in the biosynthesis of the aminocyclitol antibiotic validamycin A. This dedicated 'pseudoglycosyltransferase' catalyzes a condensation between GDP-valienol and validamine 7-phosphate to give validoxylamine A 7'-phosphate with net retention of the 'anomeric' configuration of the donor cyclitol in the product. The enzyme operates in sequence with a phosphatase, which dephosphorylates validoxylamine A 7'-phosphate to validoxylamine A.