O-(β-D-galactopyranosyl)-(1->4)-1,5-anhydro-D-glucitol | 19262-54-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(β-D-galactopyranosyl)-(1->4)-1,5-anhydro-D-glucitol
• 英文别名: 1,5-anhydro-4-O-β-D-galactopyranosyl-D-glucitol；1-deoxy-D-lactose；O⁴-β-D-galactopyranosyl-1,5-anhydro-D-glucitol；O⁴-β-D-Galactopyranosyl-1,5-anhydro-D-glucit；2-Deoxylaktose；Desoxylactose；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5S)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 19262-54-5
• 化学式: C₁₂H₂₂O₁₀
• 分子量: 326.301
• InChiKey: HEBVRGOICSSBQA-JVCRWLNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 O-(β-D-galactopyranosyl)-(1->4)-1,5-anhydro-D-glucitol 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以78.2%的产率得到O-(3,4-O-Isopropylidene-β-D-galactopyranosyl)-(1->4)-1,5-anhydro-D-glucitol
  参考文献：
  名称：

  Maeda, Hirokazu; Ito, Kenichi; Ishida, Hideharu, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 3, p. 387 - 406

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2',3,3',4',6,6'-七-O-乙酰基-alpha-D-乳糖基溴化物 在 palladium on activated charcoal 氢气 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 O-(β-D-galactopyranosyl)-(1->4)-1,5-anhydro-D-glucitol
  参考文献：
  名称：

  Synthesis of Deoxy Derivatives of Lactose and their Hydrolysis by beta-Galactosidase from E. Coli.

  摘要：

  Methyl 2-deoxy-alpha-lactoside, methyl 3-deoxy-beta-lactoside, 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-glucitol and the 2-deoxy and 2,3-dideoxy derivatives of 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-glucitol have been synthesized by deoxygenation of lactose derivatives at appropriate positions. Cyclohexyl beta-D-galactopyranoside has also been synthesized. All derivatives proved to be substrates for the enzyme beta-galactosidase from E. coli, but the rate of hydrolysis of the substrate analogues was strongly dependent on the nature of the aglycone.

  DOI：

  10.3891/acta.chem.scand.46-0186

文献信息

• First protection-free protocol for synthesis of 1-deoxy sugars through glycosyl dithiocarbamate intermediates
  作者：Gefei Li、Masato Noguchi、Kensuke Nakamura、Ryohei Hayasaka、Yuuki Tanaka、Shin-ichiro Shoda

  DOI：10.1016/j.tetlet.2018.08.005

  日期：2018.9

  A practical two-step synthetic process for 1-deoxy sugars has been established. The process consists of the direct introduction of a dimethyldithiocarbamate group into the anomeric center of unprotected sugars and subsequent hydrogenation in the AIBN-H3PO2-NaHCO3 system. No protecting groups are needed to synthesize 1-deoxy monosaccharides and 1-deoxy disaccharides.

  已经建立了用于1-脱氧糖的实用的两步合成方法。该方法包括将二甲基二硫代氨基甲酸酯基团直接引入未保护的糖的异头中心，然后在AIBN-H 3 PO 2 -NaHCO 3系统中进行氢化。不需要保护基来合成1-脱氧单糖和1-脱氧二糖。
• Stereoselective enzymatic galactosylation of C-glucosides
  作者：Luigi Panza、Pietro L. Chiappini、Giovanni Russo、Daniela Monti、Sergio Riva

  DOI：10.1039/a701747b

  日期：——

  The enzyme β-1,4-galactosyl transferase from bovine colostrum (GalT) is able stereoselectively to galactosylate C-glucosides (i.e. 1 and 4), precursors of stable glycoconjugate analogues, and a systematic investigation of the structural modifications at C-1 and/or C-5 of the glycosides that can be accepted by this enzyme has been undertaken, adding information to the currently accepted model of substrate binding into the GalT active site.

  牛初乳中的β-1,4-半乳糖基转移酶（GalT）能够立体选择性地半乳糖基化C-葡萄糖苷（即1和4）--稳定的糖苷类似物的前体--并对该酶可接受的糖苷的C-1和/或C-5结构修饰进行了系统研究，为目前公认的底物结合到GalT活性位点的模型增添了信息。
• 1,5-Anhydrolactitol and 1,5-Anhydromaltitol
  作者：Hewitt G. Fletcher、Leonore H. Koehler、C. S. Hudson

  DOI：10.1021/ja01179a029

  日期：1949.11.19
• [EN] CERAMIDE CONTENT INCREASING AGENTS<br/>[FR] AGENTS AUGMENTANT LA TENEUR EN CÉRAMIDES<br/>[JA] セラミド含量増加剤
  申请人：NAT UNIV CORP UNIV OF TOYAMA

  公开号：WO2017122495A1

  公开（公告）日：2017-07-20

  式(I)で表される化合物又はその医薬上許容される塩からなるセラミド分解酵素阻害剤、式(II)で表される化合物又はその医薬上許容される塩からなるセラミド合成促進剤。本発明のセラミド分解酵素阻害剤及びセラミド合成促進剤は、細胞又は皮膚におけるセラミド量を増加するため、例えば、保湿効果、シワの改善、アトピー性皮膚炎の症状改善、乾皮症の予防／改善、シミの予防、肌のタルミの改善、抗掻痒作用、メラニン生成抑制効果、バリア機能の向上、繊維芽細胞賦活効果、皮膚細胞の再生効果のために好適に用いられる。