per-O-methyl-D-fucopyranoside | 190128-31-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: per-O-methyl-D-fucopyranoside
• 英文别名: (3R,4S,5S,6R)-2,3,4,5-tetramethoxy-6-methyloxane
• CAS: 190128-31-5
• 化学式: C₁₀H₂₀O₅
• 分子量: 220.266
• InChiKey: FHJGOJSYFDDBAA-CYNREMDZSA-N

物化性质

• 沸点：
  261.7±40.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.42
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  在 盐酸 、 silver carbonate 作用下， 反应 2.0h， 生成 methyl 2,3,4-tri-O-methyl-L-rhamnopyranoside 、 per-O-methyl-D-fucopyranoside 、 新鲁斯可皂苷元
  参考文献：
  名称：

  Watanabe, Yoshiaki; Sanada, Shuichi; Ida, Yoshiteru, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 6, p. 1980 - 1990

  摘要：

  DOI：

文献信息

• Rapid synthesis of partially O-methylated alditol acetate standards for GC–MS: some relative activities of hydroxyl groups of methyl glycopyranosides on Purdie methylation
  作者：Guilherme L. Sassaki、Philip A.J. Gorin、Lauro M. Souza、Phelipe A. Czelusniak、Marcello Iacomini

  DOI：10.1016/j.carres.2005.01.020

  日期：2005.3

  Mixtures containing the majority of partially O-methylated alditol acetates (PMAAs), necessary for the GC-MS based identification of glycosidic linkages in oligo- and polymeric structures were prepared. Rha, Fuc, Rib, Ara, Xyl, Man, Gal, and Glc were converted to their Me glycosides, and the products were progressively O-methylated using the Purdie reagent at 25 degrees C. Resulting PMGs were assayed by TLC and at times that were optimum for formation of mono-O-methyl derivatives and later for higher degrees of methylation; they were converted to PMAAs, in a process incorporating (NaBH4)-H-2 reduction. The majority of these can be used as standards for simultaneous identification of pyranosides and some furanosyl units particularly in heteropolysaccharides. The relative reactivities of OH-groups were determined by GC-MS as: Me alpha- and beta-Glcp, HO-2 > HO-4 > HO-3 > HO-6, Me alpha- and beta-Galp, HO-3 > HO-2 > HO-4 > HO-6, Me alpha-Manp, HO-3 > HO-2 > HO-4 > HO-6, Me beta-Manp, HO-3 > HO-4 >= HO-6 > HO-2, Me alpha-Rhap, OH-3 > OH-2 > OH-4; Me alpha beta-Fucp, OH-2 > OH-3 > OH-4, and Me alpha beta-Xylp, OH-2 > OH-4 > OH-3. The results differ from those obtained with Haworth, Hakomori, and Ciucanu methylation techniques, although some similarities occurred with the more rapid Kuhn method. (c) 2005 Elsevier Ltd. All rights reserved.
• IORIZZI, MARIA;MINALE, LUIGI;RICCIO, RAFFAELE, GAZZ. CHIM. ITAL., 120,(1990) N, C. 147-153
  作者：IORIZZI, MARIA、MINALE, LUIGI、RICCIO, RAFFAELE

  DOI：——

  日期：——
• DAURIA, M. VALERIA;IORIZZI, MARIA;MINALE, LUIGI;RICCIO, RAFFAELE, J. CHEM. SOC. PT 1. PERKIN TRANS.,(1990) N, C. 1019-1023
  作者：DAURIA, M. VALERIA、IORIZZI, MARIA、MINALE, LUIGI、RICCIO, RAFFAELE

  DOI：——

  日期：——