6-azido-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid | 408360-23-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-azido-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid
• 英文别名: (2R,3S,4S,5R)-6-azido-2,3,4,5-tetramethoxyhexanoic acid
• CAS: 408360-23-6
• 化学式: C₁₀H₁₉N₃O₆
• 分子量: 277.277
• InChiKey: CARJPYBNWKMAQS-RYPBNFRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  88.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-azido-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 水 为溶剂， 反应 4.0h， 以96%的产率得到6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid
  参考文献：
  名称：

  立体酰胺的关键前体6-氨基-6-脱氧-2,3,4,5-四-O-甲基-D-半乳糖醛酸的合成

  摘要：

  标题化合物（17）是通过两个替代序列合成的，从D-半乳糖二丙酮化物（1）和甲基6 - O-甲苯磺酰基-α- D-吡喃半乳糖苷（9）开始。化合物1被转化为6-溴-6-脱氧衍生物2或被甲磺化为3。用叠氮化钠对2和3中的离去基团进行亲核取代，生成6-叠氮基6-脱氧衍生物4，在酸性条件下用甲醇处理后，得到相应的甲基β-呋喃糖苷（5）和α-吡喃糖苷（6）。的游离羟基基团的甲基化5和6，得到相应的per- ø -甲基衍生物7和8。为了在序列中维持糖环的大小，可替代地由9通过乙酰化，叠氮化物取代和过-O-甲基化制备化合物8。糖苷水解，然后氧化并进一步5- O-甲基化，得到6-叠氮基-6-脱氧羧酸16，其通过叠氮化物官能团的氢解转化为17（从9得到的总产率为38％）。

  DOI：

  10.1081/car-100108283
• 作为产物：
  描述：

  6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-D-galactopyranose 在 氢氧化钾 、 水 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 17.0h， 生成 6-azido-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid
  参考文献：
  名称：

  立体酰胺的关键前体6-氨基-6-脱氧-2,3,4,5-四-O-甲基-D-半乳糖醛酸的合成

  摘要：

  标题化合物（17）是通过两个替代序列合成的，从D-半乳糖二丙酮化物（1）和甲基6 - O-甲苯磺酰基-α- D-吡喃半乳糖苷（9）开始。化合物1被转化为6-溴-6-脱氧衍生物2或被甲磺化为3。用叠氮化钠对2和3中的离去基团进行亲核取代，生成6-叠氮基6-脱氧衍生物4，在酸性条件下用甲醇处理后，得到相应的甲基β-呋喃糖苷（5）和α-吡喃糖苷（6）。的游离羟基基团的甲基化5和6，得到相应的per- ø -甲基衍生物7和8。为了在序列中维持糖环的大小，可替代地由9通过乙酰化，叠氮化物取代和过-O-甲基化制备化合物8。糖苷水解，然后氧化并进一步5- O-甲基化，得到6-叠氮基-6-脱氧羧酸16，其通过叠氮化物官能团的氢解转化为17（从9得到的总产率为38％）。

  DOI：

  10.1081/car-100108283

文献信息

• Synthesis of stereoregular poly-O-methyl-d- and l-polygalactonamides as nylon 6 analogues
  作者：Carmen L. Romero Zaliz、Oscar Varela

  DOI：10.1016/j.tetasy.2004.11.061

  日期：2005.1

  Conveniently activated dimers: (pentachlorophenyl 6-(6'-(tert-butoxycarbonylamino)-6'-deoxy-2',3',4',5',-tetra-O-methyl-D-galactonamide)-6'-deoxy-2,3,4,5-tetra-O-methyl-D-galactonate) 7 and its analogue in the L-series 16. were prepared: respectively, from 6-amino-6-deoxy-D- and L-galactonic acid derivatives 5 and 14. Upon release of the amino function of 7 under acidic conditions, polymerization was conducted in a non-polar (CHCl3) or a polar solvent (DMF) affording poly(6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid) 11. Similarly, polymerization in DMF from 16 gave the polygalactonamide 18 (L-series). The polyamides were characterized by IR and NMR spectroscopies. The latter technique was also employed for establishing the conformation of 11 in CDCl3 solution. Molecular weights (about 11,000) were estimated by viscosimetry and size exclusion chromatography. Polygalactonamides 11 and 18 were highly hygroscopic and soluble in a variety, of organic solvents. including chloroform. The thermal behavior of the polyamides was also studied. (C) 2004 Elsevier Ltd. All rights reserved.
• Straightforward synthesis of derivatives of d- and l-galactonic acids as precursors of stereoregular polymers
  作者：Carmen L. Romero Zaliz、Oscar Varela

  DOI：10.1016/s0957-4166(03)00588-3

  日期：2003.9

  High yielding routes for the synthesis of selectively protected derivatives Of D- and L-galactonic acids. having free OH or NH2 groups at the C-6 position, are reported. The successful direct per-O-methylation of galactonic acid derivatives from the corresponding galactono- 1.4-lactones was developed as a key step of the sequence. For example. 6-azido-6-deoxy-L-galactono- 1.4-lactone 16 was converted into the potassium salt and methylated (NaH, DMSO, Mel) to the methyl ester of the 2,3.4,5-tetra-O-methyl derivative 12. Compound 16 was readily prepared by bromination at C-6 Of L-galactonolactone 1 and isopropylidenation followed by substitution of bromine by azide and removal of the protecting groups. Hydrolysis of the methyl ester of 12 and hydrogenation of the azide led to the tetra-O-methyl derivative of the 6-amino acid 18 with 52% overall yield from 1. The same sequence applied to D-galactonolactone 19 led to the enantiomeric amino acid 25 with a 47% overall yield. (C) 2003 Elsevier Ltd. All rights reserved.
• SYNTHESIS OF 6-AMINO-6-DEOXY-2,3,4,5- TETRA-O-METHYL-D-GALACTONIC ACID, A KEY PRECURSOR OF A STEREOREGULAR POLYAMIDE1
  作者：Carmen Zaliz、Oscar Varela

  DOI：10.1081/car-100108283

  日期：——

  α-pyranoside (6). Methylation of the free hydroxyl groups of 5 and 6 gave the respective per-O-methyl derivatives 7 and 8. In order to maintain the size of the sugar ring during the sequence, compound 8 was alternatively prepared from 9, by acetylation, substitution by azide and per-O-methylation. Hydrolysis of the glycoside followed by oxidation and further 5-O-methylation afforded the 6-azido-6-deoxy carboxylic

  标题化合物（17）是通过两个替代序列合成的，从D-半乳糖二丙酮化物（1）和甲基6 - O-甲苯磺酰基-α- D-吡喃半乳糖苷（9）开始。化合物1被转化为6-溴-6-脱氧衍生物2或被甲磺化为3。用叠氮化钠对2和3中的离去基团进行亲核取代，生成6-叠氮基6-脱氧衍生物4，在酸性条件下用甲醇处理后，得到相应的甲基β-呋喃糖苷（5）和α-吡喃糖苷（6）。的游离羟基基团的甲基化5和6，得到相应的per- ø -甲基衍生物7和8。为了在序列中维持糖环的大小，可替代地由9通过乙酰化，叠氮化物取代和过-O-甲基化制备化合物8。糖苷水解，然后氧化并进一步5- O-甲基化，得到6-叠氮基-6-脱氧羧酸16，其通过叠氮化物官能团的氢解转化为17（从9得到的总产率为38％）。