(2S,3R,4S)-2,3,4,5-tetrahydroxy-2,3:4,5-di-O-isopropylidene-1-C-(2-thiazolyl)-1-pentanone | 192753-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S)-2,3,4,5-tetrahydroxy-2,3:4,5-di-O-isopropylidene-1-C-(2-thiazolyl)-1-pentanone
• 英文别名: [(4S,5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-(1,3-thiazol-2-yl)methanone
• CAS: 192753-67-6
• 化学式: C₁₄H₁₉NO₅S
• 分子量: 313.375
• InChiKey: URMOTYCPAPVZLC-JMJZKYOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  95.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S)-2,3,4,5-tetrahydroxy-2,3:4,5-di-O-isopropylidene-1-C-(2-thiazolyl)-1-pentanone 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 1.67h， 生成 1,2,3,4-bis-O-(1-methylethylidene)-5-O-(phenylmethyl)-5-C-2-thiazolyl-(5S)-D-xylitol
  参考文献：
  名称：

  Carbohydrate Homologation by the Use of 2-(Trimethylsilyl)thiazole. Preparative Scale Synthesis of Rare Sugars:  l-Gulose, l-Idose, and the Disaccharide Subunit of Bleomycin A₂

  摘要：

  The well established one-carbon homologation method of protected monosaccharides employing 2-(trimethylsilyl)thiazole (2-TST) as a formyl anion equivalent has been used for high yield and multigram scale synthesis of the title rare hexoses from L-xylose. Thus, L-gulose has been obtained by stereoselective anti-addition of 2-TST to aldehydo-L-xylose diacetonide followed by thiazole to formyl conversion of the resulting alcohol. The inversion of configuration at C-1 of this alcohol by an oxidation-reduction sequence prior to the aldehyde releasing from thiazole led to L-idose. The same alcohol was readily elaborated into 1,3,4,6-tetra-O-acetyl-L-gulopyranose whose highly stereoselective glycosidation coupling with 3-O-carbamoyl-2,4,6-tri-O-acetyl-alpha-D-mannosyl diethyl phosphate afforded the same peracetylated disaccharide subunit employed by Boger and Honda in the total synthesis of the antibiotic bleomycin A(2).

  DOI：

  10.1021/jo970601h
• 作为产物：
  描述：

  在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (2S,3R,4S)-2,3,4,5-tetrahydroxy-2,3:4,5-di-O-isopropylidene-1-C-(2-thiazolyl)-1-pentanone
  参考文献：
  名称：

  Carbohydrate Homologation by the Use of 2-(Trimethylsilyl)thiazole. Preparative Scale Synthesis of Rare Sugars:  l-Gulose, l-Idose, and the Disaccharide Subunit of Bleomycin A₂

  摘要：

  The well established one-carbon homologation method of protected monosaccharides employing 2-(trimethylsilyl)thiazole (2-TST) as a formyl anion equivalent has been used for high yield and multigram scale synthesis of the title rare hexoses from L-xylose. Thus, L-gulose has been obtained by stereoselective anti-addition of 2-TST to aldehydo-L-xylose diacetonide followed by thiazole to formyl conversion of the resulting alcohol. The inversion of configuration at C-1 of this alcohol by an oxidation-reduction sequence prior to the aldehyde releasing from thiazole led to L-idose. The same alcohol was readily elaborated into 1,3,4,6-tetra-O-acetyl-L-gulopyranose whose highly stereoselective glycosidation coupling with 3-O-carbamoyl-2,4,6-tri-O-acetyl-alpha-D-mannosyl diethyl phosphate afforded the same peracetylated disaccharide subunit employed by Boger and Honda in the total synthesis of the antibiotic bleomycin A(2).

  DOI：

  10.1021/jo970601h

文献信息

• Carbohydrate Homologation by the Use of 2-(Trimethylsilyl)thiazole. Preparative Scale Synthesis of Rare Sugars:  <scp>l</scp>-Gulose, <scp>l</scp>-Idose, and the Disaccharide Subunit of Bleomycin A₂
  作者：Alessandro Dondoni、Alberto Marra、Alessandro Massi

  DOI：10.1021/jo970601h

  日期：1997.9.1

  The well established one-carbon homologation method of protected monosaccharides employing 2-(trimethylsilyl)thiazole (2-TST) as a formyl anion equivalent has been used for high yield and multigram scale synthesis of the title rare hexoses from L-xylose. Thus, L-gulose has been obtained by stereoselective anti-addition of 2-TST to aldehydo-L-xylose diacetonide followed by thiazole to formyl conversion of the resulting alcohol. The inversion of configuration at C-1 of this alcohol by an oxidation-reduction sequence prior to the aldehyde releasing from thiazole led to L-idose. The same alcohol was readily elaborated into 1,3,4,6-tetra-O-acetyl-L-gulopyranose whose highly stereoselective glycosidation coupling with 3-O-carbamoyl-2,4,6-tri-O-acetyl-alpha-D-mannosyl diethyl phosphate afforded the same peracetylated disaccharide subunit employed by Boger and Honda in the total synthesis of the antibiotic bleomycin A(2).