(2R,4aR,6S,9bR)-8-amino-4,4a,6,9b-tetrahydro-6-methoxy-2-phenylthieno[2',3':4,5]pyrano[3,2-d][1,3]dioxine-7-carbonitrile | 887480-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡喃类
• 英文名称: (2R,4aR,6S,9bR)-8-amino-4,4a,6,9b-tetrahydro-6-methoxy-2-phenylthieno[2',3':4,5]pyrano[3,2-d][1,3]dioxine-7-carbonitrile
• 英文别名: (1R,7S,9R,12R)-4-amino-7-methoxy-12-phenyl-8,11,13-trioxa-3-thiatricyclo[7.4.0.02,6]trideca-2(6),4-diene-5-carbonitrile
• CAS: 887480-51-5
• 化学式: C₁₇H₁₆N₂O₄S
• 分子量: 344.391
• InChiKey: YDXUHKJTNJEXBP-ZPUIDXCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6S,9bR)-8-amino-4,4a,6,9b-tetrahydro-6-methoxy-2-phenylthieno[2',3':4,5]pyrano[3,2-d][1,3]dioxine-7-carbonitrile 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (2R,4aR,6S,11bR)-4,4a,6,11b-tetrahydro-6-methoxy-2-phenyl-[1,3]dioxino[4'',5'':5',6']pyrano[3',4':4,5]thieno[2,3-d]pyrimidin-7-amine
  参考文献：
  名称：

  Synthesis of Heteroanellated Pyranosides Starting from Methyl 4,6‐O‐benzylidene‐2,3‐dideoxy‐α‐d‐erythro‐hexopyranosid‐2‐ylidenemalononitrile

  摘要：

  The hexopyranosid-2-ylidenemalononitrile 1 reacted with phenyl isothiocyanate in the presence of triethylamine to furnish (2R ,4aR ,6S ,10bS )-8-amino-4a,6,10,10b-tetrahydro-6-methoxy-2-phenyl-10-phenylimino-4 H-thiopyrano[3',4':4,5]pyrano[3,2-d][1,3]dioxine-7-carbonitrile (2). Starting from 1, cyclization with sulphur and diethylamine yielded (2R ,4aR ,6S ,9bR )-8-amino-4,4a,6,9b-tetrahydro-6-methoxy-2-phenylthieno[2',3':4,5]pyrano[3,2- d][1,3]dioxine-7-carbonitrile (3), which could be transformed into the corresponding aminomethylenamino derivative 4 by treatment with triethyl orthoformate and ammonia. Intramolecular cyclization of 4 to yield (2R ,4aR ,6S ,11b R )-4,4a,6,11b-tetrahydro-6-methoxy-2-phenyl[1,3]dioxino[4?,5?:5',6']pyrano[3',4':4,5]thieno [2,3- d ]pyrimidin-7-amine (5) was achieved by using NaH as base. (2R ,4aR ,6S ,9bS)-8-Amino-4a,6,9,9b-tetrahydro-6-methoxy-9-(4-methylphenyl-sulfonyl)-2-phenyl-4 H -[1,3]dioxino[4',5':5,6]pyrano[4,3- b]pyrrole-7-carbonitrile (6) was prepared by treatment of compound 1 with tosylazide and triethylamine.

  DOI：

  10.1080/07328300500495852
• 作为产物：
  描述：

  Methyl 4,6-O-benzylidene-2-(dicyanomethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 二乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以69%的产率得到(2R,4aR,6S,9bR)-8-amino-4,4a,6,9b-tetrahydro-6-methoxy-2-phenylthieno[2',3':4,5]pyrano[3,2-d][1,3]dioxine-7-carbonitrile
  参考文献：
  名称：

  Synthesis of Heteroanellated Pyranosides Starting from Methyl 4,6‐O‐benzylidene‐2,3‐dideoxy‐α‐d‐erythro‐hexopyranosid‐2‐ylidenemalononitrile

  摘要：

  The hexopyranosid-2-ylidenemalononitrile 1 reacted with phenyl isothiocyanate in the presence of triethylamine to furnish (2R ,4aR ,6S ,10bS )-8-amino-4a,6,10,10b-tetrahydro-6-methoxy-2-phenyl-10-phenylimino-4 H-thiopyrano[3',4':4,5]pyrano[3,2-d][1,3]dioxine-7-carbonitrile (2). Starting from 1, cyclization with sulphur and diethylamine yielded (2R ,4aR ,6S ,9bR )-8-amino-4,4a,6,9b-tetrahydro-6-methoxy-2-phenylthieno[2',3':4,5]pyrano[3,2- d][1,3]dioxine-7-carbonitrile (3), which could be transformed into the corresponding aminomethylenamino derivative 4 by treatment with triethyl orthoformate and ammonia. Intramolecular cyclization of 4 to yield (2R ,4aR ,6S ,11b R )-4,4a,6,11b-tetrahydro-6-methoxy-2-phenyl[1,3]dioxino[4?,5?:5',6']pyrano[3',4':4,5]thieno [2,3- d ]pyrimidin-7-amine (5) was achieved by using NaH as base. (2R ,4aR ,6S ,9bS)-8-Amino-4a,6,9,9b-tetrahydro-6-methoxy-9-(4-methylphenyl-sulfonyl)-2-phenyl-4 H -[1,3]dioxino[4',5':5,6]pyrano[4,3- b]pyrrole-7-carbonitrile (6) was prepared by treatment of compound 1 with tosylazide and triethylamine.

  DOI：

  10.1080/07328300500495852

文献信息

• Synthesis of Heteroanellated Pyranosides Starting from Methyl 4,6‐<i>O</i>‐benzylidene‐2,3‐dideoxy‐α‐<scp>d</scp>‐<i>erythro</i>‐hexopyranosid‐2‐ylidenemalononitrile
  作者：Holger Schulz、Holger Feist、Klaus Peseke

  DOI：10.1080/07328300500495852

  日期：2006.1.1

  The hexopyranosid-2-ylidenemalononitrile 1 reacted with phenyl isothiocyanate in the presence of triethylamine to furnish (2R ,4aR ,6S ,10bS )-8-amino-4a,6,10,10b-tetrahydro-6-methoxy-2-phenyl-10-phenylimino-4 H-thiopyrano[3',4':4,5]pyrano[3,2-d][1,3]dioxine-7-carbonitrile (2). Starting from 1, cyclization with sulphur and diethylamine yielded (2R ,4aR ,6S ,9bR )-8-amino-4,4a,6,9b-tetrahydro-6-methoxy-2-phenylthieno[2',3':4,5]pyrano[3,2- d][1,3]dioxine-7-carbonitrile (3), which could be transformed into the corresponding aminomethylenamino derivative 4 by treatment with triethyl orthoformate and ammonia. Intramolecular cyclization of 4 to yield (2R ,4aR ,6S ,11b R )-4,4a,6,11b-tetrahydro-6-methoxy-2-phenyl[1,3]dioxino[4?,5?:5',6']pyrano[3',4':4,5]thieno [2,3- d ]pyrimidin-7-amine (5) was achieved by using NaH as base. (2R ,4aR ,6S ,9bS)-8-Amino-4a,6,9,9b-tetrahydro-6-methoxy-9-(4-methylphenyl-sulfonyl)-2-phenyl-4 H -[1,3]dioxino[4',5':5,6]pyrano[4,3- b]pyrrole-7-carbonitrile (6) was prepared by treatment of compound 1 with tosylazide and triethylamine.