allyl O-(α-D-glucopyranosyl)-(1->4)-O-(α-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside | 149300-02-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl O-(α-D-glucopyranosyl)-(1->4)-O-(α-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside
• 英文别名: allyl O-α-D-glucopyranosyl-(1<*>4)-O-α-D-glucopyranosyl-(1<*>4)-β-D-glucopyranoside；Glc(a1-4)Glc(a1-4)Glc(b)-O-allyl；(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-prop-2-enoxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 149300-02-7
• 化学式: C₂₁H₃₆O₁₆
• 分子量: 544.507
• InChiKey: ANMSPHYBVLGPLO-NBYRGYPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.7
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  258
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 allyl O-(α-D-glucopyranosyl)-(1->4)-O-(α-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside 在 sodium hydride 作用下， 生成 allyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  All-α-d-linked tetra- and penta-saccharide substructures of Trestatin A by block syntheses with triflic anhydride as promoter

  摘要：

  The perbenzylated maltosyl and maltotriosyl fluorides 6 and 16 were treated with 2,3,2',3',6'-penta-O-benzyl-4,6-O-benzylidene-alpha,alpha-trehalose (7) using triflic anhydride as a promoter to give all-alpha-D-linked tetra- and penta-saccharides which were finally deblocked to the free oligosaccharides 4-O-alpha-maltosyl- 9 and 4-O-alpha-maltotriosyl-alpha,alpha-trehaloses 18. The H-1 NMR spectra of some of the compounds were fully analyzed by 1D TOCSY and ROESY experiments.

  DOI：

  10.1016/0008-6215(93)80028-d
• 作为产物：
  描述：

  maltotriose peracetate 在 乙酰溴 、 sodium methylate 、 silver carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 allyl O-(α-D-glucopyranosyl)-(1->4)-O-(α-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  使用立体选择性脱水糖基化合成具有α(1→4)和α(1→6)键的含葡萄糖线性低聚糖

  摘要：

  使用立体选择性脱水糖基化与对硝基苯磺酰基试剂混合物合成具有 α(1→4) 和 α(1→6) 键的 D-葡萄糖的与糖原储存相关的线性四糖、六糖和八糖氯化物、三氟甲磺酸银、N,N-二甲基乙酰胺和三乙胺。准化学计量量的八糖供体和受体交叉缩合，然后脱保护，得到葡糖十六糖。

  DOI：

  10.1246/bcsj.68.2331

文献信息

• Synthesis of Glucose-Containing Linear Oligosaccharides Having<i>α</i>(1→4) and<i>α</i>(1→6) Linkages Using Stereoselective Dehydrative Glycosylation
  作者：Shinkiti Koto、Hisamitsu Haigoh、Sonoko Shichi、Motoko Hirooka、Teiko Nakamura、Chika Maru、Misuzu Fujita、Ayano Goto、Tomoko Sato、Masato Okada、Shonosuke Zen、Kazuo Yago、Fumiya Tomonaga

  DOI：10.1246/bcsj.68.2331

  日期：1995.8

  g linear tetra-, hexa-, and octasaccharides of D-glucose having α(1→4) and α(1→6) linkages were synthesized using a stereoselective dehydrative glycosylation with a reagent mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine. A cross-condensation of a quasi-stoichiometric amount of a donor and an acceptor of an octasaccharide, followed

  使用立体选择性脱水糖基化与对硝基苯磺酰基试剂混合物合成具有 α(1→4) 和 α(1→6) 键的 D-葡萄糖的与糖原储存相关的线性四糖、六糖和八糖氯化物、三氟甲磺酸银、N,N-二甲基乙酰胺和三乙胺。准化学计量量的八糖供体和受体交叉缩合，然后脱保护，得到葡糖十六糖。
• All-α-d-linked tetra- and penta-saccharide substructures of Trestatin A by block syntheses with triflic anhydride as promoter
  作者：Hans Peter Wessel、Beatrice Mayer、Gerhard Englert

  DOI：10.1016/0008-6215(93)80028-d

  日期：1993.4

  The perbenzylated maltosyl and maltotriosyl fluorides 6 and 16 were treated with 2,3,2',3',6'-penta-O-benzyl-4,6-O-benzylidene-alpha,alpha-trehalose (7) using triflic anhydride as a promoter to give all-alpha-D-linked tetra- and penta-saccharides which were finally deblocked to the free oligosaccharides 4-O-alpha-maltosyl- 9 and 4-O-alpha-maltotriosyl-alpha,alpha-trehaloses 18. The H-1 NMR spectra of some of the compounds were fully analyzed by 1D TOCSY and ROESY experiments.