(1R,2S,3R,6R)-6-氨基环己-4-烯-1,2,3-三醇 | 142796-97-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R,2S,3R,6R)-6-氨基环己-4-烯-1,2,3-三醇
• 中文别名: 二磷酸)三氢8-溴腺苷5'-(
• 英文名称: (-)-conduramine C₁
• 英文别名: (1R,2S,3R,6R)-6-Aminocyclohex-4-ene-1,2,3-triol
• CAS: 142796-97-2
• 化学式: C₆H₁₁NO₃
• 分子量: 145.158
• InChiKey: RAJLHDDMNNFKNT-KAZBKCHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (1R,2S,3R,6R)-6-氨基环己-4-烯-1,2,3-三醇 在 吡啶 作用下， 反应 15.0h， 生成 (1R,2S,3R,4R)-4-(acetamido)cyclohex-5-ene-1,2,3-triyl triacetate
  参考文献：
  名称：

  （-）-conduramine C 1和氨基溴环糖醇衍生物的对映选择性合成†

  摘要：

  （1 S，2 R，6 R，7 R）-4-苯基-3,10-二氧杂-5-氮杂三环[5.2.1.0 2,6 ] dec-4-en-9-one（（+）- 5从呋喃的Diels-Alder加合物到1-氰基乙烯基（1 S）-樟脑酸酯（（+）- 3）的6个步骤中获得的）被还原为相应的内醇（-）- 6，用HBr /提供的AcOH（-）-（3a S，4 S，6 R，7 S，7a R）-4β-溴-3aβ，4,5,6,7,7aβ-六氢-2-苯基-1,3-苯并恶唑-6β，7α-二乙酸二乙酯（（-）- 17）。用1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）消除HBr，并进行酸性水解，得到（-）-（1 R，2 S，3 R，4 R）-4-氨基环己基-5-烯-1,2,3-三醇（（-）-conduramine C 1 ;（-）- 1）。

  DOI：

  10.1002/hlca.19940770103
• 作为产物：
  描述：

  (1R,2R,6S,7R,8S)-4,4-Dimethyl-8-(toluene-4-sulfonyl)-3,5-dioxa-10-aza-tricyclo[5.2.1.02,6]decane-10-carboxylic acid tert-butyl ester 在 盐酸 、 甲醇 、 disodium hydrogenphosphate 、 sodium amalgam 、 正丁基锂 、 氨 、 双氧水 、 碳酸氢钠 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 49.25h， 生成 (1R,2S,3R,6R)-6-氨基环己-4-烯-1,2,3-三醇
  参考文献：
  名称：

  Synthesis of Conduramines from N-tert-Butoxycarbonylpyrrole

  摘要：

  Two related synthetic strategies were devised to convert the Diels-Alder adduct 3c of Boc-pyrrole and p-toluenesulfonylacetylene into various racemic and optically pure conduramines. One process consists of the regio-and stereoselective hydroxylation of 3c to the tri-and dihydroxylated azabicyclo[2.2.1]heptane derivatives 10b (Scheme 2) and the exo-endo mixture 13-14 (Scheme 3). Anionic fragmentation of 10b (methylmagnesium bromide) and of the 13-14 sulfone mixture (lithium bis(trimethylsilyl)amide) generated the corresponding tri-and dihydroxylated aminocyclohexenes 17 and 16 (Scheme 3). Compound 17 is an aminocyclitol with a stereochemistry and partial aminotriol sequence identical to that found in neoinosamine. Compound 16 served as a source of the protected and fi ee aminodiols 35b, and 35a (Scheme 6), which were stereospecifically epoxidized to 36 (Scheme 6) and 40 (Scheme 7). Phenylselenide cleavage of these epoxides provided 37 (Scheme 6) and 41a (Scheme 7), which after selenoxide cycloelimination and protecting group manipulation were converted into (+/-)-conduramine C-l (39a, Scheme 6) and the previously unreported, all-cis-conduramine D-l (43a, Scheme 7). In a second process, anionic fragmentaion of the bicyclic system is effected prior to introduction of the hydroxyl groups, as exemplified by the high-yielding conversion of the exo-endo mixture of azabicycloheptenes 11 and 12 into the aminocyclohexadiene 15 (Scheme 3). Osmate catalyzed cis-dihydroxylation of the derived bis-Boc derivative 20 (Scheme 4) Zed stereospecifically to the alpha-cis-diol 21 which was transformed into (+/-)-conduramine A-1 (27a) and its tetraacetyl derivative 27b via the epoxy compound 24. On the other hand, peracid oxidation of the diene 15 gave the beta-epoxide 28 (Scheme 5) which was cleaved to the trans-diol 29 with aqueous sulfuric acid. This diol was converted into (+/-)-conduramine F-1(34a) and its tetraacetyl derivative (34b) by a reaction sequence similar to that used for the other conduramine syntheses. Fractional crystallization of the diastereomeric mixture of Michael adducts obtained from (+/-)-3c and (-)methyl lactate gave (-)-44a and (-)-45a both in greater than or equal to 47% yield (Scheme 8). Both the carboxylic acid (+)-44b and the primary alcohol (+)-46 derived from (-)-44a were converted into (-)-3c with excess methylmagnesium bromide (ca. 40% overall yield). In the same way (-)-45a was transformed into optically pure (+)-3c. (-)-3c and (+)-3c were then converted into (-)-conduramine C-l [(-)-39a] and (+)-conduramine D-l [(+)-43a] by procedures identical to those used for the racemic compounds.

  DOI：

  10.1021/jo971907r