(1R,2R,6S)-2-Methoxy-7-(toluene-4-sulfonyl)-3-oxa-7-aza-bicyclo[4.2.0]octane-5,8-dione | 211182-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R,6S)-2-Methoxy-7-(toluene-4-sulfonyl)-3-oxa-7-aza-bicyclo[4.2.0]octane-5,8-dione
• CAS: 211182-87-5
• 化学式: C₁₄H₁₅NO₆S
• 分子量: 325.342
• InChiKey: RNZOBPGWVIIICM-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  89.98
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙氧甲酰基亚甲基三苯基膦 、 (1R,2R,6S)-2-Methoxy-7-(toluene-4-sulfonyl)-3-oxa-7-aza-bicyclo[4.2.0]octane-5,8-dione 以 甲苯 为溶剂， 反应 8.0h， 以58%的产率得到3-[(R)-2-Methoxy-5-oxo-4-(toluene-4-sulfonylamino)-tetrahydro-pyran-3-yl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid ethyl ester
  参考文献：
  名称：

  Formation of β-lactams fused to the pyranoid ring via the Mitsunobu reaction

  摘要：

  N-Tosyl-2-C-carbamoyl glycosides having the alpha-L-arabino- and beta-D-xylo- configuration form under Mitsunobu conditions 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-alpha-L-lyxo and beta-D-arabinopyranosides, respectively, having the beta-lactam ring fused to the pyranoid one; neither the formation of the gamma-lactam ring nor that of the 3,4-epoxide were observed. The gamma-lactam 2-C:4-N-carbonyl-2,4-dideoxy-4-N-tosylamino-beta-D-xylopyranoside can be obtained after protection of the 3-hydroxy group in the starting glycoside of alpha-L-arabino-configuration. The structure and configuration of methyl 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-beta-D-ribopyranoside and methyl 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-beta-D-erythro-pyranosid-4-ulose were proved by X-ray crystallography. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00017-2
• 作为产物：
  描述：

  (((3R,4R)-3,4-dihydro-2H-pyran-3,4-diyl)bis(oxy))bis(trimethylsilane) 在 盐酸 、 ruthenium(IV) oxide 、 sodium periodate 、 苄基三乙基氯化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 8.25h， 生成 (1R,2R,6S)-2-Methoxy-7-(toluene-4-sulfonyl)-3-oxa-7-aza-bicyclo[4.2.0]octane-5,8-dione
  参考文献：
  名称：

  Formation of β-lactams fused to the pyranoid ring via the Mitsunobu reaction

  摘要：

  N-Tosyl-2-C-carbamoyl glycosides having the alpha-L-arabino- and beta-D-xylo- configuration form under Mitsunobu conditions 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-alpha-L-lyxo and beta-D-arabinopyranosides, respectively, having the beta-lactam ring fused to the pyranoid one; neither the formation of the gamma-lactam ring nor that of the 3,4-epoxide were observed. The gamma-lactam 2-C:4-N-carbonyl-2,4-dideoxy-4-N-tosylamino-beta-D-xylopyranoside can be obtained after protection of the 3-hydroxy group in the starting glycoside of alpha-L-arabino-configuration. The structure and configuration of methyl 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-beta-D-ribopyranoside and methyl 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-beta-D-erythro-pyranosid-4-ulose were proved by X-ray crystallography. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00017-2