allyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-β-D-glucopyranoside | 131267-29-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enoxyoxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 131267-29-3
• 化学式: C₅₇H₆₂O₁₁
• 分子量: 923.113
• InChiKey: KBHJITYOEPNLMD-BDJXAYMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.16
• 重原子数：
  68.0
• 可旋转键数：
  25.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112.53
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  allyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.33h， 生成
  参考文献：
  名称：

  Synthesis of structural elements of the capsular polysaccharide of streptococcus pneumoniae type 8

  摘要：

  The synthesis is reported of propyl 4-O-alpha-D-galactopyranosyl-beta-D-glucopyranosiduronic acid (25), 4-O-[4-O-(beta-D-glucopyranosyluronic acid)-beta-D-glucopyranosyl]-D-glucopyranose (34), and 4-O-(4-O-beta-D-glucopyranosyl-alpha-D-glucopyranosyl)-D-galactopyranose (38), each representing a structural element of the repeating unit of the capsular polysaccharide of Streptococcus pneumoniae type 8, [-->4)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->4)-alpha-D-Glcp-(1-->4)-alpha-D-Galp-(1-->]n. 2,3-Di-O-benzyl-4,6-O-benzylidene-alpha-D-galactopyranosyl trichloroacetimidate (12) was coupled to allyl 2-0-acetyl-3-O-benzyl-6-0-trityl-beta-D-glucopyranoside (7) in dichloromethane-ether, using trimethylsilyl trifluoromethanesulfonate as a promoter, to give disaccharide derivative 20. Detritylation of 20, followed by oxidation and deprotection, afforded disaccharide propyl glycoside 25. Coupling of 2,3,4,6-tetra-0-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (8) to allyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside (17) in dichloromethane, with trimethylsilyl trifluoromethanesulfonate as a promoter, resulted in trisaccharide derivative 26. Deacetylation of 26, followed by 6-O-tritylation, benzylation, detritylation, and oxidation gave a protected trisaccharide derivative (31), which, after deprotection, afforded 34. Coupling of allyl 2,3,6-tri-O-benzyl-beta-D-galactopyranoside (10) to 4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate (19) in ether, with trimethylsilyl trifluoromethanesulfonate as a promoter, gave trisaccharide derivative 35. Deallylation of 35, followed by hydrogenolysis afforded 38.

  DOI：

  10.1016/s0040-4020(01)82378-4
• 作为产物：
  描述：

  allyl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside 在 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 allyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  寡糖的合成：丙基O-β-d-吡喃半乳糖基-（1→2）-O-α-d-吡喃吡喃糖基-（1→6）-O-β-d-吡喃葡萄糖基-（1→4）-的化学合成β-d-吡喃葡萄糖苷

  摘要：

  摘要在二氯甲烷存在下，烯丙基3,4-二-O-苄基-β-d-吡喃吡喃糖苷与2-O-乙酰基-3,4,6-三-O-苄基-α-d-吡喃半乳糖酰氯在二氯甲烷中缩合。三氟甲磺酸银产生烯丙基2-O-（2-O-乙酰基-3,4,6-三-O-苄基-β-d-吡喃半乳糖基）-3,4-二-O-苄基-β-d-吡喃吡喃糖苷（ 7，83％）。化合物7经五步转化为2-O-（2-O-乙酰基-3,4,6-三-O-苄基-β-d-吡喃半乳糖基）-3,4-二-O-苄基-α- d-吡喃基吡喃糖基溴化物（13），立即与烯丙基2 2,3,6-tri-O-乙酰基-4-O-（2,3-di-O-乙酰基-β-d-吡喃吡喃糖基）-β缩合-d-吡喃葡萄糖苷得到结晶烯丙基O-（2-O-乙酰基-3,4,6-三-O-苄基-β-d-吡喃半乳糖基）-（1→2）-O-（3,4-di -O-苄基-α-d-吡喃吡喃糖基）-（1→6）-O-（2,3-二-O-乙酰基-β-d-吡喃吡喃糖基）-（1→4）-2

  DOI：

  10.1016/0008-6215(90)80143-q

文献信息

• Oligosaccharide Analogues of Polysaccharides. Part 26
  作者：Kadiyala V. S. N. Murty、Tong Xie、Bruno Bernet、Andrea Vasella

  DOI：10.1002/hlca.200690068

  日期：2006.4

  cellulose I, and the ethynyl and buta-1,3-diynyl linker units ensure an appropriate phase shift between them. The H-bonding of the T-x-x mimics was analysed and compared to the one of the mono-chained analogues T-x and of the known cellulose II mimics N-x-x and N-x where one or two cellodextrin chains are O-glycosidically bonded to naphthalene-1,8-diethanol, or to naphthalene-1-ethanol. The OH signals of

  蒽醌衍生物Txx（x  = 2、4和8）分别具有两个纤维二糖基，纤维四糖基和纤维八糖基链，在C（1）和C（8）上键合的C-糖苷被合成为纤维素I的潜在模拟物。蒽醌模板在与纤维素I的晶体学独立链之间的距离相对应的距离上，使纤维糊精链平行取向，并且乙炔基和1,3-二乙炔基连接基团确保它们之间的适当相移。分析了Txx模拟物的H键并与单链类似物Tx和已知的纤维素II模拟物Nxx和Nx之一进行了比较其中一个或两个纤维糊精链通过O-糖基键合到萘1,8-二乙醇或萘-1-乙醇上。根据DQFCOSY，HSQC和TOCSY（仅​​适用于T-4，T-4-4和T-8-8）光谱以及根据DQFCOSY，HSQC和TOCSY分配（D 6）DMSO中溶液中Tx和Txx的OH信号与Nx和Nxx的光谱进行比较。根据OH基团的化学位移及其温度依赖性，偶联常数，SIMPLE 1 H-NMR实验和ROESY光谱对氢键进行了分析。T-4-4和T-8-8
• Oligosaccharide Analogues of Polysaccharides, Part 19, Synthesis of 2-(Naphthalen-1-yl)ethyl Cellooligoglycosides and [(Naphthalene-1,8-diyl)di(ethane-2,1-diyl)] Bis[cellooligoglycosides]
  作者：Jinwang Xu、Andrea Vasella

  DOI：10.1002/(sici)1522-2675(19991006)82:10<1728::aid-hlca1728>3.0.co;2-a

  日期：1999.10.6