3,7-dideoxy-D-gluco-heptono-1,4-lactone | 116498-80-7

• 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: 3,7-dideoxy-D-gluco-heptono-1,4-lactone
• 英文别名: (3R,5R)-5-[(1R,2R)-1,2-dihydroxypropyl]-3-hydroxyoxolan-2-one
• CAS: 116498-80-7
• 化学式: C₇H₁₂O₅
• 分子量: 176.169
• InChiKey: TUGNLHHZHMDJAK-KVTDHHQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 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：

  3,7-dideoxy-D-gluco-heptono-1,4-lactone 在 吡啶 、 camphor-10-sulfonic acid 、 甲基磺酰氯 作用下， 反应 3.0h， 生成 (3S,5R)-3-Chloro-5-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-dihydro-furan-2-one
  参考文献：
  名称：

  Highly Functionalized Cyclopentanes by Radical Cyclization of Unsaturated Bromolactones. 2. A Facile Synthesis of the First Carbaaldohexofuranoses and Their Conversion to Carbapentofuranoses

  摘要：

  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.

  DOI：

  10.1021/jo971928l
• 作为产物：
  描述：

  (3R,4R,5R)-5-((4S,5S)-5-Bromomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-dihydro-furan-2-one 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 97.0h， 生成 3,7-dideoxy-D-gluco-heptono-1,4-lactone
  参考文献：
  名称：

  Highly Functionalized Cyclopentanes by Radical Cyclization of Unsaturated Bromolactones. 2. A Facile Synthesis of the First Carbaaldohexofuranoses and Their Conversion to Carbapentofuranoses

  摘要：

  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.

  DOI：

  10.1021/jo971928l

文献信息

• d-glycero-d-gulo-Heptono-1,4-lactone as a precursor for the synthesis of deoxyheptonolactones and anhydroheptonolactones
  作者：Klaus Bock、Inge Lundt、Christian Pedersen、Richardt Sonnichsen

  DOI：10.1016/0008-6215(88)85102-4

  日期：1988.3

  Abstract Hydrogenolysis of d - glycero - d - gulo -heptono-1,4-lactone penta-acetate gave 3-deoxy- d - gluco -heptonolactone tetra-acetate, which was converted easily into methyl 3-deoxy- d - gluco -heptonate and, thence, into 7-bromo-3,7-dideoxy- and 3,7- dideoxy- d - gluco -heptono-1,4-lactone. Reaction of d - glycero - d - gulo -heptono-1,4-lactone ( 4a ) with hydrogen bromide—acetic acid gave 2

  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。
• BOCK, KLAUS;LUNDT, INGE;PEDERSEN, CHRISTIAN;SONNICHSEN, RICHARDT, CARBOHYDR. RES., 174,(1988) 331-340
  作者：BOCK, KLAUS、LUNDT, INGE、PEDERSEN, CHRISTIAN、SONNICHSEN, RICHARDT

  DOI：——

  日期：——
• 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.