O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-manno-hexopyranosyl)-(1->4)-1-O-acetyl-3-azido-2,3,6-tridesoxy-α-L-arabino-hexopyranose | 127444-70-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-manno-hexopyranosyl)-(1->4)-1-O-acetyl-3-azido-2,3,6-tridesoxy-α-L-arabino-hexopyranose
• 英文别名: [(2S,4S,5R,6S)-4-azido-5-[(2S,3R,4R,5S,6S)-4,5-diacetyloxy-3-iodo-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl] acetate
• CAS: 127444-70-6
• 化学式: C₁₈H₂₆IN₃O₉
• 分子量: 555.324
• InChiKey: SINLKQPLRBTFDT-XELDXFLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  155.35
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-manno-hexopyranosyl)-(1->4)-1-O-acetyl-3-azido-2,3,6-tridesoxy-α-L-arabino-hexopyranose 在 水 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-manno-hexopyranosyl)-(1->4)-1-O-acetyl-2,3,6-tridesoxy-3-trifluoroacetamido-α-L-arabino-hexopyranose
  参考文献：
  名称：

  Synthèse de disaccharides polydésoxygénés et iodés

  摘要：

  3-Amino-polydeoxy disaccharides have been prepared by condensation of a glycal with methyl 2,3,6-trideoxy-alpha-L-erythro- (or threo)-hex-2-enopyranoside in the presence of N-iodosuccinimide. After acid hydrolysis of the glycoside, 1,4-addition of hydrazoic acid to the corresponding hex-2-enopyranose led to 3-azido-disaccharides which were acetylated. Reduction of the azido group gave 2,2'-dideoxy- or 2,2'-dideoxy-2'-iodo compounds. Condensation of O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-alpha-L-manno-hexopyranosyl)-(1 --> 4)-1-O-acetyl-2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-arabino-hexopyranose with daunomycinone, followed by 3',4'-O-deacetylation produced the new anthracycline, 7-O-[O-(2,6-dideoxy-2-iodo-alpha-L-manno-hexopyranosyl)-(1 --> 4)-2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-arabino-hexopyranosyl]-daunomycinone.

  DOI：

  10.1016/s0008-6215(00)90558-5
• 作为产物：
  描述：

  methyl-O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-manno-hexopyranosyl)-(1->4)-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranoside 在 吡啶 、 sodium azide 、 溶剂黄146 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 O-(3,4-di-O-acetyl-2,6-didesoxy-2-iodo-α-L-manno-hexopyranosyl)-(1->4)-1-O-acetyl-3-azido-2,3,6-tridesoxy-α-L-arabino-hexopyranose
  参考文献：
  名称：

  Synthèse de disaccharides polydésoxygénés et iodés

  摘要：

  3-Amino-polydeoxy disaccharides have been prepared by condensation of a glycal with methyl 2,3,6-trideoxy-alpha-L-erythro- (or threo)-hex-2-enopyranoside in the presence of N-iodosuccinimide. After acid hydrolysis of the glycoside, 1,4-addition of hydrazoic acid to the corresponding hex-2-enopyranose led to 3-azido-disaccharides which were acetylated. Reduction of the azido group gave 2,2'-dideoxy- or 2,2'-dideoxy-2'-iodo compounds. Condensation of O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-alpha-L-manno-hexopyranosyl)-(1 --> 4)-1-O-acetyl-2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-arabino-hexopyranose with daunomycinone, followed by 3',4'-O-deacetylation produced the new anthracycline, 7-O-[O-(2,6-dideoxy-2-iodo-alpha-L-manno-hexopyranosyl)-(1 --> 4)-2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-arabino-hexopyranosyl]-daunomycinone.

  DOI：

  10.1016/s0008-6215(00)90558-5

文献信息

• A new route to 4-epi- L -daunosamine containing disaccharides
  作者：Belgacem Abbaci、Jean-Claude Florent、Claude Monneret

  DOI：10.1039/c39890001896

  日期：——

  The methyl 4-O-(2,6-dideoxy-2-iodo-α-L-mannopyranosyl)-α-L-acosaminide (11) and the methyl 4-O-(2,6-dideoxy-α-L-arabinopyranosyl)-α-L-acosaminide analogue (12) have been stereoselectively synthesized in seven and eight steps, respectively, from di-O-acetyl-L-rhamnal (4) and methyl 2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside (5); the key step involved a 1,4-addition of hydrazoic acid to a corresponding

  甲基4- ø - （2,6-二脱氧-2-碘- α-大号-mannopyranosyl）-α-大号-acosaminide（11）和4- ø - （2,6-二脱氧α-大号-阿拉伯糖基）-α-大号-acosaminide类似物（12）已经在七个，八步骤中被立体选择性合成，分别从二ö乙酰基大号-rhamnal（4）和甲基-2,3,6-三脱氧-α-α-大号-赤-hex-2-烯吡喃糖苷（5）；关键步骤涉及将1，4-肼基酸加成到相应的hex-2-enopyranose。
• ABBACI, BELGACEM;FLORENT, JEAN-CLAUDE;MONNERET, CLAUDE, J. CHEM. SOC. CHEM. COMMUN.,(1989) N4, C. 1896-1897
  作者：ABBACI, BELGACEM、FLORENT, JEAN-CLAUDE、MONNERET, CLAUDE

  DOI：——

  日期：——