methyl 6-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranoside | 122926-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl 6-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranoside
• 英文别名: [(3aS,4R,6R,7R,7aS)-7-acetyloxy-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl acetate
• CAS: 122926-88-9
• 化学式: C₁₄H₂₂O₈
• 分子量: 318.324
• InChiKey: YBBXOTRLSAKQLF-KSSYENDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 6-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranoside 在 三氟乙酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.08h， 以3 g的产率得到Methyl 2,6-di-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Glycosylation by sugar 1,2-O-(1-cyanobenzylidene) derivatives: influence of glycosyl-donor structure and promoter

  摘要：

  3,4,6-Tri-O-acetyl-1,2-O-(1-cyanobenzylidene)-alpha-D-galactopyranoses with differently substituted aromatic nuclei have been synthesised and used as glycosyl donors in reactions with the acceptors methyl 2,3,4-tri-O-acetyl-6-O-trityl-beta-D-galactopyranoside (11) and methyl 2,4,6-tri-O-acetyl-3-O-trityl-beta-D-galactopyranoside (12). The glycosylation of 11 gave only beta products. The efficiency and stereoselectivity of the glycosylations of 12 depend on the nature of the substituent in the aromatic ring. The stereoselectivity for the formation of 1,2-trans-glycosidic bonds was the highest with the p-methoxy-benzylidene derivative with triphenylmethylium triflate as the promoter.

  DOI：

  10.1016/0008-6215(93)80006-z
• 作为产物：
  描述：

  methyl 3,4-di-O-isopropylidene-β-D-galactopyranoside 生成 methyl 6-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  BETANELI, V. I.;KRYAZHEVSKIX, I. A.;OTT, A. YA.;KOCHETKOV, N. K., BIOORGAN. XIMIYA, 15,(1989) N, S. 217-230

  摘要：

  DOI：

文献信息

• Efficient Acetylation of Carbohydrates Promoted by Imidazole
  作者：Pallavi Tiwari、Rishi Kumar、Prakas R. Maulik、Anup Kumar Misra

  DOI：10.1002/ejoc.200500555

  日期：2005.10

  An efficient per-O-acetylation of carbohydrate derivatives and unprotected reducing sugars promoted by imidazole is reported. The reaction conditions have been successfully employed to acetylate carbohydrate derivatives containing acid-susceptible functional groups. In most of the cases the yields obtained were excellent. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  据报道，由咪唑促进的碳水化合物衍生物和未受保护的还原糖的有效过-O-乙酰化。该反应条件已成功用于乙酰化含有酸敏感官能团的碳水化合物衍生物。在大多数情况下，获得的产率非常好。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Efficient acylation and sulfation of carbohydrates using sulfamic acid, a mild, eco-friendly catalyst under organic solvent-free conditions
  作者：Abhishek Santra、Goutam Guchhait、Anup Kumar Misra

  DOI：10.1039/c1gc15122c

  日期：——

  fast and efficient acylation of carbohydrate derivatives and free sugars using a stoichiometric quantity of acylating agents in the presence of sulfamic acid, an environmentally benign catalyst, under organic solvent-free conditions is reported. Excellent yields in the selective acylation and sulfation of carbohydrate derivatives have also been achieved using sulfamic acid as the catalyst. The reaction

  快速高效 酰化 的 碳水化合物衍生物 在存在以下条件下，使用化学计量的酰化剂制备游离糖和游离糖 氨基磺酸，对环境无害 催化剂，在有机 溶剂-无条件的报道。选择性的酰化和硫酸化硫酸具有优异的收率碳水化合物衍生物 也已经通过使用 氨基磺酸 作为 催化剂。反应速度快，收率优异。
• Tandem Acetalation−Acetylation of Sugars and Related Derivatives with Enolacetates under Solvent-Free Conditions
  作者：Debaraj Mukherjee、Bhahwal Ali Shah、Pankaj Gupta、Subhash Chandra Taneja

  DOI：10.1021/jo070363i

  日期：2007.11.1

  [GRAPHICS]Molecular iodine catalyzes acetalation and acetylation of reducing sugars and sugar glycosides with stoichiometric amounts of enol acetates under solvent-free conditions, thereby facilitating the synthesis of various types of orthogonally protected sugar derivatives in short time and good yields. The outcome of the reaction can be controlled by variation in temperature. Thus at lower temperature, it is possible to obtain the acetonide acetate as a single product whereas peracetate is the major product at higher temperature.
• Structure elucidation of methyl 3,4-O-isopropylidene-α- and -β-D-galactopyranosides by NMR and X-ray analysis
  作者：Pier Luigi Barili、Giorgio Catelani、Giancarlo Fabrizi、Doriano Lamba

  DOI：10.1016/0008-6215(93)84088-n

  日期：1993.4
• Efficient Differentiation of the Hydroxyl Groups of 3,4-<i>O</i>-Isopropylidene-D-Galactopyranosides by Lipase Catalyzed Esterification and De - Esterification
  作者：Pier Luigi Barili、Giorgio Catelani、Felicia D'Andrea、Ettore Mastrorilli

  DOI：10.1080/07328309708005733

  日期：1997.9

  The Pseudomonas sp. (LPS) promoted acyl transfer from vinyl acetate to selected 3,4-O-isopropylidene-D-galactopyranosides takes place in a completely selective manner giving in high yield the corresponding 6-O-acetates. The acetylation rate is strongly dependent on the type and the orientation of the aglycon, varying from a maximum of reactivity for the 1-deoxy derivative, 1,5-anhydro-3,4-O-isopropylidene-D-galactitol (1d), to a minimum for beta configurated alkyl glycosides and showing a complete loss of reactivity for 3',4':2,3:5,6-tri-O-isopropylidenelactose dimethyl acetal (1e). The latter compound is, however, selectively 6'-O-esterified in good yield by lipase from Candida Antarctica and vinyl acetate. Also the course of the enzymatic hydrolysis of 2,6-di-O-acetyl-3,4-O-isopropylidene-D-galactopyranosides 2 is dependent on the type of the aglycon, both for the reaction rate and the selectivity. The 2-O-acetates 4 are selectively obtained in good yields with porcine pancreatic lipase (PPL) promoted hydrolysis in the case of beta- and alpha-methyl, and 1-deoxy derivatives (2a, 2b and 2d), while for beta-benzyl (2c) and lactose (2e) analogues satisfactory results are obtained with lipase from Mucor miehei (IM20).