Methyl (R)-2-<4-(2,2-dimethyl-1,3-dioxolanyl)>thiazole-4-carboxylate | 85622-44-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Methyl (R)-2-<4-(2,2-dimethyl-1,3-dioxolanyl)>thiazole-4-carboxylate
• 英文别名: methyl 2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-thiazole-4-carboxylate
• CAS: 85622-44-2
• 化学式: C₁₀H₁₃NO₄S
• 分子量: 243.284
• InChiKey: JODJMFXUNCEKTM-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl (R)-2-<4-(2,2-dimethyl-1,3-dioxolanyl)>thiazole-4-carboxylate 在 4-二甲氨基吡啶 、 sodium hydroxide 、 camphor-10-sulfonic acid 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 Dolabellin
  参考文献：
  名称：

  Dolabellin, a Cytotoxic Bisthiazole Metabolite from the Sea Hare Dolabella auricularia: Structural Determination and Synthesis

  摘要：

  Dolabellin (1), a novel cytotoxic metabolite which consists of two thiazole hydroxy acids and a new dichlorinated beta-hydroxy acid, was isolated from the Japanese sea hare Dolabella auricularia. The gross structure of 1 was elucidated on the basis of spectral data in conjunction with chemical degradations, which provided three methyl esters: methyl 2-(1-hydroxy-2 -methylpropyl)thiazole-4-carboxylate (2), methyl 2-(1,2-dihydroxyethyl)thiazole-4-carboxylate (3), and methyl 7,7-dichloro-3-hydroxy-2-methyloctanoate (4). The absolute stereochemistry of 1 was determined by stereoselective syntheses of two degradation products 2 and 3 and two diastereomeric octanoates 7a,b (the dechloro derivatives of degradation product 4), and the enantioselective total synthesis of dolabellin itself. Dechlorodolabellin (23) was also synthesized.

  DOI：

  10.1021/jo00120a021
• 作为产物：
  描述：

  Dolabellin 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 26.0h， 生成 Methyl (R)-2-<4-(2,2-dimethyl-1,3-dioxolanyl)>thiazole-4-carboxylate
  参考文献：
  名称：

  Dolabellin, a Cytotoxic Bisthiazole Metabolite from the Sea Hare Dolabella auricularia: Structural Determination and Synthesis

  摘要：

  Dolabellin (1), a novel cytotoxic metabolite which consists of two thiazole hydroxy acids and a new dichlorinated beta-hydroxy acid, was isolated from the Japanese sea hare Dolabella auricularia. The gross structure of 1 was elucidated on the basis of spectral data in conjunction with chemical degradations, which provided three methyl esters: methyl 2-(1-hydroxy-2 -methylpropyl)thiazole-4-carboxylate (2), methyl 2-(1,2-dihydroxyethyl)thiazole-4-carboxylate (3), and methyl 7,7-dichloro-3-hydroxy-2-methyloctanoate (4). The absolute stereochemistry of 1 was determined by stereoselective syntheses of two degradation products 2 and 3 and two diastereomeric octanoates 7a,b (the dechloro derivatives of degradation product 4), and the enantioselective total synthesis of dolabellin itself. Dechlorodolabellin (23) was also synthesized.

  DOI：

  10.1021/jo00120a021

文献信息

• A FACILE SYNTHETIC APPROACH TO THE FRAGMENT D OF ANTIBIOTIC NOSIHEPTIDE, 2-[1-AMINO-3-CARBOXY-3-HYDROXY-(1<i>S</i>,3<i>S</i>)-PROPYL]-THIAZOLE-4-CARBOXYLIC ACID
  作者：Masaharu Iwakawa、Yasunobu Kobayashi、Shun-ichi Ikuta、Juji Yoshimura

  DOI：10.1246/cl.1982.1975

  日期：1982.12.5

  The lactam corresponding to fragment D of a polypeptide antibiotic nosiheptide was prepared via oxidation of the corresponding thiazolidine-4-carboxylate obtained by the condensation of 2-azido-2,3-dideoxy-d-threo-pentoalduronate with l-cysteine methyl ester.

  对应于多肽抗生素那西肽片段D的内酰胺是通过氧化相应的噻唑烷-4-羧酸盐来制备的，该噻唑烷-4-羧酸盐是通过2-叠氮基-2,3-二脱氧-d-苏-戊糖醛酸与L-半胱氨酸甲酯缩合获得的。