1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside | 18685-22-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• 英文别名: octa-O-benzyl-sucrose；octabenzyl saccharose；octa-O-benzylsucrose；octabenzyl sucrosa；1,3,4,6-Tetra-O-benzyl-β-D-fructosyl-2,3,4,6-tetra-O-benzyl-4a-D-glucosid；(2R,3R,4S,5R,6R)-2-[(2S,3S,4R,5R)-3,4-bis(phenylmethoxy)-2,5-bis(phenylmethoxymethyl)oxolan-2-yl]oxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 18685-22-8
• 化学式: C₆₈H₇₀O₁₁
• 分子量: 1063.3
• InChiKey: FWXRDTYENUXNOM-QQHZVUSNSA-N

物化性质

• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  79
• 可旋转键数：
  29
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 在 氢气 三氟甲磺酸 、 trifluoromethanesulfonic acid anhydride 作用下， 以 二氯甲烷 为溶剂， 生成 1,3,4,6,1',3',4',6'-octa-O-benzyl-β-D-fructofuranosyl-β-D-fructofuranoside
  参考文献：
  名称：

  Pavia, Andre A.; Ung-Chhun, Sak N., Canadian Journal of Chemistry, 1981, vol. 59, p. 482 - 490

  摘要：

  DOI：
• 作为产物：
  描述：

  Ethyl 1,3,4,6-tetra-O-benzoyl-2-thio-D-fructofuranoside 在 N-碘代丁二酰亚胺 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.5h， 生成 1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of d-Fructofuranosides Using Thioglycosides as Glycosyl Donors

  摘要：

  Benzylated and benzoylated ethyl thioglycosides of D-fructofuranose have been synthesized and tested as glycosyl donors in couplings to various primary and secondary carbohydrate accepters. Treatment of 2-O-acetyl-1,3,4,6-tetra-O-benzoyl-D-fructofuranose with ethyl mercaptan in a BF3 .-etherate-promoted reaction gave the benzoylated ethyl 2-thio-alpha,beta-D-fructofuranosides, which after deacylation and benzylation afforded the benzylated derivatives. These thiofructofuranosides, using dimethyl(methylthio)sulfonium triflate (DMTST) or N-iodosuccinimide as promoter, were found to be excellent donors, which gave disaccharide coupling products in quantitative or almost quantitative yields with all tested accepters, yields rarely found in oligosaccharide synthesis. The benzoylated donors gave only alpha-linked fructofuranosides, due to participation of the 3-O-benzoyl group, whereas the benzylated donors gave alpha/beta-mixtures.

  DOI：

  10.1021/jo951641t

文献信息

• Convenient Syntheses of 2,3,4,6-Tetra-O-AlkylatedD-Glucose andD-Galactose
  作者：Ludwig Käsbeck、Horst Kessler

  DOI：10.1002/jlac.199719970124

  日期：1997.1

  Convenient syntheses of the 2,3,4,6-tetra-O-benzylated and -allylated D-glucopyranoses 1 and 2 and the corresponding D-galactopyranoses 3 and 4 are described. The D-glucose derivatives 1 and 2 were obtained from inexpensive sucrose by peralkylation and subsequent acid hydrolysis. In this reaction sequence an alkylated D-fructofuranosyl cation is generated which was trapped by different nucleophiles

  描述了2,3,4,6-四-O-苄基化和烯丙基化的D-吡喃葡萄糖1和2以及相应的D-吡喃半乳糖3和4的方便的合成。D-葡萄糖衍生物1和2是从廉价的蔗糖中通过过烷基化和随后的酸水解获得的。在该反应序列中，产生烷基化的D-果糖呋喃糖基阳离子，该阳离子被不同的亲核试剂捕获，得到4-苄氧基亚甲基糠醛（8）和烷基化的D-果糖苷7、8和10。另一方面，2,3,4,6-四-O-苄基-D-半乳糖3通过用N-溴代琥珀酰亚胺水溶液氧化裂解乙基2,3,4,6-四-O-苄基-1-硫代-α，β-D-吡喃半乳糖苷（11）来合成。通过对甲氧基苄基β-D-葡糖苷制备2,3,4,6-四-O-烯丙基-D-吡喃葡萄糖苷（2）的替代途径吸引力较小。然而，被用于的2,3,4,6-四-合成此路线ö -allyl- d半乳糖（4）。
• Synthesis of raffinose family oligosaccharides by regioselective de-O-benzylation with Co2(CO)8/Et3SiH/CO system
  作者：Yue-tao Zhao、Shan Niu、Lu-bai Huang、Ji-ming Wang、Zhao-jun Yin、Qing Li、Zhong-jun Li

  DOI：10.1016/j.tet.2013.03.094

  日期：2013.6

  key step is the regioselective de-O-benzylation with Co2(CO)8/Et3SiH/CO system, followed by a high α-selective glycosylation. The newly developed de-O-benzylation system is efficient in removing the primary benzyl groups of sucrose and raffinose under mild condition and with high selectivity. Using thioglycoside as donor, NIS/AgOTf as promoter and DTBMP as additive, glycosylation of acid labile sucrose

  提出了一种方便的方法，以蔗糖为原料合成棉子糖，水苏糖和马齿c糖。关键步骤是使用Co 2（CO）8 / Et 3 SiH / CO系统进行区域选择性脱O-苄基化，然后进行高水平的α-选择性糖基化。新开发的脱-O-苄基化系统可在温和条件下以高选择性高效去除蔗糖和棉子糖的伯苄基。使用硫代糖苷作为供体，NIS / AgOTf作为启动子，DTBMP作为添加剂，酸不稳定蔗糖底物的糖基化可以实现高收率。
• Preparation of partially benzylated mono-, di-, and trisaccharides by selective cleavage of the β-fructofuranosidic linkage in fully benzylated sucrose and sucrose-related oligosaccharides under acidic conditions
  作者：Takashi Yamanoi、Noriko Misawa、Sho Matsuda、Mikio Watanabe

  DOI：10.1016/j.carres.2008.03.024

  日期：2008.6

  Several partially benzylated mono-, di-, and trisaccharides having an anomeric hydroxyl group were successfully prepared by selective cleavage of the beta-fructofuranosidic linkage in fully benzylated sucrose and sucrose-related oligosaccharides derived from lactosucrose, raffinose, melezitose, stachyose, and nystose under acidic conditions using 1:10 75% aqueous sulfuric acid-dioxane at room temperature

  通过选择性地在完全苄基化的蔗糖和衍生自乳糖蔗糖，棉子糖，松三糖，水苏糖和核糖的蔗糖相关的低聚糖中，β-果糖呋喃糖苷键的选择性裂解，成功制备了具有异头羟基的部分部分苄基化的单糖，二糖和三糖在酸性条件下，使用1:10 75％硫酸-二恶烷水溶液在室温下放置1h。
• 1,3,4,6-tetra-O-benzyl-d-fructofuranose and some of its derivatives
  作者：Robert K. Ness、Harry W. Diehl、Hewitt G. Fletcher

  DOI：10.1016/s0008-6215(00)84891-0

  日期：1970.4

  -fructofuranose derivative has been further characterized through the preparation of a p -nitrobenzoate, a p -phenylazobenzoate and a benzoate — all crystalline derivatives. To confirm the structure of 4 , it was also made through the hydrolysis of octa- O -benzylsucrose and by the partial oxidation of 1,3,4,6-tetra- O -benzyl- d -mannitol ( 11 ); the preparation of 11 and of two crystalline derivatives therefrom

  摘要通过以下步骤，由d-果糖获得了晶体1,3,4,6-四-O-苄基-d-果糖呋喃糖（4），总收率为60％。 d-果糖呋喃糖苷→4。通过制备对-硝基苯甲酸酯，对-苯偶氮苯甲酸酯和苯甲酸酯（均为结晶衍生物），进一步表征了新的d-果糖呋喃糖衍生物。为了证实4的结构，它还通过八-O-苄基蔗糖的水解和1,3,4,6-四-O-苄基-d-甘露糖醇的部分氧化制得（11）。描述了由其制备11和两种结晶衍生物的方法。
• Szeja, W.; Fokt, I.; Grynkiewicz, G., Recueil des Travaux Chimiques des Pays-Bas, 1989, vol. 108, # 6, p. 224 - 226
  作者：Szeja, W.、Fokt, I.、Grynkiewicz, G.

  DOI：——

  日期：——