methyl 4R,3-benzyl-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylate | 1311981-39-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 4R,3-benzyl-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylate
• 英文别名: N-benzyl-D-serine methyl ester sulfamidate；methyl (4R)-3-benzyl-2,2-dioxooxathiazolidine-4-carboxylate
• CAS: 1311981-39-1
• 化学式: C₁₁H₁₃NO₅S
• 分子量: 271.294
• InChiKey: SEERWJZPOLYZDW-SNVBAGLBSA-N

物化性质

• 沸点：
  396.2±52.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4R,3-benzyl-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylate 、 N-叔丁基氧羰基-L-组氨酸甲酯 在 potassium dihydrogenphosphate 、 水 作用下， 以 乙二醇二甲醚 为溶剂， 反应 7.0h， 以57%的产率得到dimethyl Nα-tert-butoxycarbonyl-Nα'-benzyl-τ-L-histidino-D-alaninate
  参考文献：
  名称：

  Synthesis of Histidinoalanine: A Comparison of β-Lactone and Sulfamidate Electrophiles

  摘要：

  Previous syntheses of histidinoalanine (HAL) have led to mixtures of regioisomers and/or stereoisomers. For example, opening of N-Cbz-D-serine-beta-lactone (6) with Boc-L-His-OMe (5) gave a 2:1 mixture of tau- and pi-regioisomers. The sulfamidate 10, derived from N-benzyl-D-serine methyl ester (11), was reacted with Boc-L-His-OMe (5) to give the tau-HAL derivative 17 as a single isomer in 57% yield. A similarly prepared tau-HAL 19, bearing protecting groups that were all hydrogenolytically labile, led to the free bis-amino acid, tau-L-histidinyl-D-alanine (tau-4), as a salt-free standard for amino acid analysis.

  DOI：

  10.1021/jo200744d
• 作为产物：
  描述：

  D-N-苄基丝氨酸甲酯 在 吡啶 、 sodium periodate 、 氯化亚砜 、 ruthenium(III) chloride trihydrate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.59h， 生成 methyl 4R,3-benzyl-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylate
  参考文献：
  名称：

  Synthesis of Histidinoalanine: A Comparison of β-Lactone and Sulfamidate Electrophiles

  摘要：

  Previous syntheses of histidinoalanine (HAL) have led to mixtures of regioisomers and/or stereoisomers. For example, opening of N-Cbz-D-serine-beta-lactone (6) with Boc-L-His-OMe (5) gave a 2:1 mixture of tau- and pi-regioisomers. The sulfamidate 10, derived from N-benzyl-D-serine methyl ester (11), was reacted with Boc-L-His-OMe (5) to give the tau-HAL derivative 17 as a single isomer in 57% yield. A similarly prepared tau-HAL 19, bearing protecting groups that were all hydrogenolytically labile, led to the free bis-amino acid, tau-L-histidinyl-D-alanine (tau-4), as a salt-free standard for amino acid analysis.

  DOI：

  10.1021/jo200744d

文献信息

• Total Synthesis of Aspergillomarasmine A and Related Compounds: A Sulfamidate Approach Enables Exploration of Structure-Activity Relationships
  作者：Silvia A. Albu、Kalinka Koteva、Andrew M. King、Salma Al-Karmi、Gerard D. Wright、Alfredo Capretta

  DOI：10.1002/anie.201606657

  日期：2016.10.10

  secondary metabolite aspergillomarasmine A (AMA) has recently been identified as an inhibitor of metallo‐β‐lactamases NDM‐1 and VIM‐2. Described herein is an efficient and practical route to AMA and its related compounds by a sulfamidate approach. In addition, a series of derivatives has been prepared and tested for biological activity in an effort to explore preliminary structure activity relationships.

  真菌次生代谢物曲霉葡糖胺A（AMA）最近被确定为金属β-内酰胺酶NDM-1和VIM-2的抑制剂。本文描述了通过氨基磺酸盐方法制备AMA及其相关化合物的有效且实用的途径。另外，已经准备了一系列衍生物并对其生物学活性进行了测试，以探索初步的结构活性关系。虽然已确定AMA的天然LLL异构体仍然是体外和细胞中NDM-1酶活性最有效的灭活剂，但该结构对3、6和9位立体化学变化的耐受性很高。