2,7-dibromo-2,7-dideoxy-D-glycero-D-ido-heptono-1,4-lactone | 116386-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2,7-dibromo-2,7-dideoxy-D-glycero-D-ido-heptono-1,4-lactone
• 英文别名: (3S,4R,5S)-3-bromo-5-[(1R,2S)-3-bromo-1,2-dihydroxypropyl]-4-hydroxyoxolan-2-one
• CAS: 116386-12-0
• 化学式: C₇H₁₀Br₂O₅
• 分子量: 333.961
• InChiKey: WGGCIWYPWNFBCB-RDQKPOQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,7-dibromo-2,7-dideoxy-D-glycero-D-ido-heptono-1,4-lactone 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 氢氟酸 为溶剂， 反应 96.0h， 生成 3,6-anhydro-2,7-dideoxy-L-ido-heptono-1,4-lactone
  参考文献：
  名称：

  d-甘油-d-gulo-Heptono-1,4-内酯为合成脱氧庚内酯和脱水庚内酯的前体

  摘要：

  摘要d-甘油-d-gulo-庚酮-1,4-内酯五乙酸酯的氢解反应制得3-脱氧-d-葡萄糖-庚内酯四乙酸酯，该酯易于转化为3-脱氧-d-葡萄糖-庚酸甲酯。因此，形成7-溴-3,7-二脱氧-和3,7-二脱氧-d-葡萄糖-庚-1,4-内酯。d-甘油-d-gulo-庚-1,4-内酯（4a）与溴化氢-乙酸的反应生成2,7-二溴-2,7-二脱氧-d-甘油-d-偶氮-heptono-1 ，4-内酯（5），其氢解得到7-溴-2,7-二脱氧-（7），2,7-二脱氧-（8）或7-溴-2,3,7-三苯氧基-庚基。 -1,4-内酯（9），取决于条件。将5在水中加热时，得到2,5：4,7-双脱水-d-甘油-d-gulo-庚酸。4a与甲酸在氟化氢中反应生成3,6-脱水-1-甘油-d-古洛-庚酮-1的混合物，4-内酯和3,7-脱水-d-甘油-d-古洛-庚-1,4-内酯。类似的处理将7和8转化为3，6-酐。

  DOI：

  10.1016/0008-6215(88)85102-4
• 作为产物：
  描述：

  葡庚糖酸内酯 在 氢溴酸 、 溶剂黄146 作用下， 反应 1.0h， 生成 2,7-dibromo-2,7-dideoxy-D-glycero-D-ido-heptono-1,4-lactone
  参考文献：
  名称：

  具有来自 L-Gulono-1,4-内酯和 D-Glycero-D-gulo-heptano-1,4-内酯的呋喃、吡喃诺和 Septano 基序的脱氧硫糖衍生物

  摘要：

  从 L-gulono-1,4-内酯和 D-glucoheptono-1,4-内酯开始，已经实现了模拟呋喃糖、吡喃糖和七糖结构的硫糖衍生物的短合成。合成中使用的不同策略是：（1）亲核置换和迈克尔加成；(2)环氧化物开环和迈克尔加成；(3)环氧化物开环亲核​​置换过程；(4) 双亲核置换。所有这些反应都使用四硫代钼酸苄基三乙基铵，(BnEt3N)(2)MoS4 作为硫转移试剂。

  DOI：

  10.1002/ejoc.201200906

文献信息

• Preparation of Enantiomerically Pure Mono- and Diepoxylactones from Aldonolactones
  作者：Inge Lundt、Christian Pedersen

  DOI：10.1055/s-1992-26196

  日期：——

  Treatment of bromodeoxyaldonolactones with a nonaqueous base, such as potassium fluoride, caesium fluoride or potassium carbonate in acetone, yields 2,3-anhydro-, 5,6-anhydro-, and 2,3: 5,6-dianhydrohexonolactones, or 2,3-anhydro-and 2,3:6,7-dianhydrohepto-nolactones in good yields.

  用非水基（如丙酮中的氟化钾、氟化铯或碳酸钾）处理溴代脱氧己内酯，可得到 2,3-脱水、5,6-脱水和 2,3：5,6-二氢己内酯或 2,3-脱水-2,3:6,7-二氢七内酯，收率良好。
• Deoxyiminoalditols from Aldonolactones; IV: Preparation of 1,5-Dideoxy-1,5-iminoheptitols with L-glycero-D-manno, D-glycero-L-gulo and L-glycero-D-altro Configuration
  作者：Inge Lundt、Robert Madsen

  DOI：10.1055/s-1995-4009

  日期：1995.7

  Three novel 1,5-dideoxy-1,5-iminoheptitols 4, 12 and 20 were prepared by a convenient two-step procedure from 2,7-dibromo-2,7-dideoxyheptono-1,4-lactones 1, 9 and 17, respectively. The dibromolactones were either reacted directly with ammonia to give iminoheptonic acids which were then reduced, or the dibromolactones were first reduced to dibromoheptitols which were then treated with ammonia. The ring closure of the dibromo compounds was shown to proceed via epoxides. In addition, chain elongation of D-mannose and D-galactose with cyanide was carried out and the resulting heptonic acids were used for preparation of four novel bromodeoxyheptonolactones 6, 9, 14 and 17.

  通过方便的两步程序，由 2,7-二溴-2,7-二脱氧庚酮-1,4-内酯 1、9 和 17 制备了三种新型 1,5-二脱氧-1,5-亚氨基庚醇 4、12 和 20 ， 分别。二溴内酯直接与氨反应得到亚氨基庚酸，然后将其还原，或者二溴内酯首先还原为二溴庚醇，然后用氨处理。显示二溴化合物的闭环是通过环氧化物进行的。此外，用氰化物对D-甘露糖和D-半乳糖进行扩链，所得庚酸用于制备四种新型溴脱氧庚酸内酯6、9、14和17。
• Highly functionalised cyclopentanes by radical cyclisation of unsaturated bromolactones. I preparation of 5-Deoxycarbahexofuranoses
  作者：Anne Marie Horneman、Inge Lundt

  DOI：10.1016/s0040-4020(97)00319-0

  日期：1997.5

  3-Unsaturated 7-bromo-7-deoxy-heptono-1,4-lactones were prepared by reductive elimination of the starting compounds. The key step was a highly regio- and stereoselective 5-exo-trig radical cyclisation of the unsaturated bromolactones to give bicyclic cyclopentane derivatives. The lactone moiety of these compounds were reduced using H3B · S(CH3)2 to give the above-mentioned carbahexofuranoses.

  三个carbasugars：5- Deoxycarba-α-L-木糖-hexofuranose，5- deoxycarba-α-L-来苏-hexofuranose和5- deoxycarba-β-D-来苏-hexofuranose已经制备从容易获得的2,7-二溴开始-2,7-二脱氧-D-甘油-D-碘-庚-1,4-内酯和2,7-二溴-2,7-二脱氧-D-甘油-L-葡萄糖-庚-1,4-内酯。通过还原性消除起始化合物来制备2，3-不饱和的7-溴-7-脱氧-庚基-1，4-内酯。关键步骤是高度区域选择性和立体选择性5- exo-触发不饱和溴内酯的自由基环化，得到双环环戊烷衍生物。用H 3 B·S（CH 3）2还原这些化合物的内酯部分，得到上述的呋喃并呋喃呋喃糖酶。
• Highly Functionalized Cyclopentanes by Radical Cyclization of Unsaturated Bromolactones. 2. A Facile Synthesis of the First Carbaaldohexofuranoses and Their Conversion to Carbapentofuranoses
  作者：Anne Marie Horneman、Inge Lundt

  DOI：10.1021/jo971928l

  日期：1998.3.1

  A novel type of carbasugars, carbaaldohexofuranoses, has been prepared using a 5-exo-trig radical cyclization of C-2 substituted 2,3-unsaturated 7-bromoheptono-1,4-lactones as the key step. During the cyclization step, two-stereogenic centers were farmed with high stereoselectivity. The lactone moieties of the cyclopentane derivatives were reduced to the alcohols, and the following carbahexofuranoses were synthesized: carba-beta-D-mannofuranose, carba-alpha-L-glucofuranose and 5-amino-5-deoxycarba-alpha-L-glucofuranose. Side chain degradation of the two former compounds gave the carbapentofuranoses: carba-alpha-L-xylofuranose and carba-beta-D-lyxofuranose.