2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide | 34339-69-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide
• 英文别名: 2,4,6-Tri-O-acetyl-3-O-benzyl-a-D-glucopyranosyl bromide；[(2R,3R,4S,5R,6R)-3,5-diacetyloxy-6-bromo-4-phenylmethoxyoxan-2-yl]methyl acetate
• CAS: 34339-69-0
• 化学式: C₁₉H₂₃BrO₈
• 分子量: 459.291
• InChiKey: CGABNHMTZHBNMO-FQBWVUSXSA-N

物化性质

• 沸点：
  501.4±50.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide 在 sodium methylate 、 silver trifluoromethanesulfonate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成 ethyl (3-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  New Factors Governing Stereoselectivity in Borohydride Reductions ofβ-D-Glycoside-2-uloses − The Peculiar Effect of “Activated” DMSO

  摘要：

  Comparative evaluation of the manno/gluco ratios obtained in the conventional reductions of beta -D-glucoside-2-uloses (1-4, 13 and 14) reveals the influence of the substitution pattern: the presence of a 4,6-O-acetal function results in lower stereoselectivity in the monosaccharide-uloside cases and low stereoselectivity in the disaccharide-uloside cases, while the absence of a 4,6-O-acetal group provides distinctly higher stereoselectivity. The 3-O-benzyl and 3-O-allyl ethers vicinal to the carbonyl to be reduced have a similar influence on the steric outcome of the carbonyl reduction. A peculiar effect of acetoxydimethylsulfonium acetate ("activated" DMSO) was observed. In all cases, its presence strongly increased the manno-selectivity of the reduction. A simple, preparatively expedient, commonly suitable protocol has been elaborated for achieving high manno-selectivities and, hence, satisfactory yields.

  DOI：

  10.1002/1099-0690(200012)2000:23<3931::aid-ejoc3931>3.0.co;2-w
• 作为产物：
  描述：

  3-O-苄基-1,2:5,6-O-双异丙叉-α-D-呋喃葡萄糖 在 吡啶 、 Amberlite IR-120 (H+ form) 、 氢溴酸 、 溶剂黄146 作用下， 反应 20.0h， 生成 2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  Synthesis of glycyrrhetic acid diglycosides and their cytoprotective activities against CCl4--induced hepatic injury in vitro

  摘要：

  Glycyrrhetic acid diglycosides 16, 24, 25, 42 and 46, with respectively beta-D-glucuronopyranosyl-(1-->3)-beta-D-glucopyranose, -(1-->6)-alpha-D-glucopyranose, -(1-->6)-beta-D-glucopyranose, -(1-->6)-beta-D-galactopyranose, and beta-D-galacturonopyranosyl-(-->2)-beta-D-glucopyranose as sugar components at the O-3 positions on the aglycons, were synthesized. In vitro cytoprotective activities, against CCl4-induced hepatic injury, of the synthetic diglycosides, methyl beta-D-glucuronopyranosyl-(1-->4)-alpha-D-glucopyranosyl-D-glycyrrhetinate 33 and methyl esters 15 and 23 (the precursors of 16 and 24 respectively) were compared with those of glycyrrhizin 1 and beta-D-glucuronopyranosyl-(1-->2)-beta-D-glucopyranosyl-glycyrrhetic acid 2. Of the glycosides 16, 24, and 25, with beta-D-glucuronopyranosyl-glucopyranose as the sugar component, 16 and 24 were as cytoprotective as 1 and 2, whereas 25 showed no remarkable activity. From stereomodels of the glycosides these differences in activity were inferred to be due to the stereochemistries of the terminal beta-D-glucuronopyranoses in the molecules. Glycoside 46, in which the terminal beta-D-glucuronopyranose of 2 was replaced by beta-D-galacturonopyranose, was as potent as 2. Further, it was confirmed that a free COOH group on the E ring of aglycon was essential for the activity.

  DOI：

  10.1016/0223-5234(96)89552-3

文献信息

• Iridoid and phenolic glycosides from Harpagophytum Procumbens
  作者：Johann F.W. Burger、E.Vincent Brandt、Daneel Ferreira

  DOI：10.1016/s0031-9422(00)81833-6

  日期：1987.4

  Abstract A novel bioside, β-(3′,4′-dihydroxyphenyl)ethyl- O -α- L -rhamnopyranosyl(1 → 3)-D-glucopyranoside, was obtained from the secondary roots of Harpagophytum procumbens . It is accompanied by the known iridoid glucosides harpagoside, procumbide, and its 6′- O -p-coumaroyl ester, and phenolic glycosides, acteoside and isoacteoside, the latter pair being obtained from H. procumbens for the first

  摘要 从Harpagophytum procumbens 的次生根中获得了一种新型生物苷β-(3',4'-二羟基苯基)乙基-O-α-L-吡喃鼠李糖基(1→3)-D-吡喃葡萄糖苷。它伴随着已知的环烯醚萜苷 harpagoside、procumbide 及其 6'-O-p-香豆酰酯，以及酚糖苷、acteoside 和 isoacteoside，后者对首次从 H. procumbens 中获得。这些代谢物的结构通过高分辨率 NMR 研究进行了区分，而生物苷的结构也得到了合成的支持。
• Photocatalytic Synthesis of Glycosyl Bromides
  作者：Weihua Xue、Xiaolong Yuan、Sen Cheng、Yanbin Shi

  DOI：10.1055/s-0033-1340493

  日期：——

  with tris(2,2′-bipyridyl)ruthenium(II) chloride as a catalyst under visible-light irradiation. Protecting groups commonly used in carbohydrate derivatives are unaffected by the mild conditions for bromination. Sugar hemiacetals were smoothly transformed into the corresponding glycosyl bromides by treatment with carbon tetrabromide in N,N-dimethylformamide with tris(2,2′-bipyridyl)ruthenium(II) chloride

  摘要 通过在可见光下用三（2,2'-联吡啶基）氯化钌（II）作催化剂的四溴化碳在N，N-二甲基甲酰胺中的处理，将糖半缩醛平稳地转化为相应的糖基溴化物。碳水化合物衍生物中常用的保护基不受温和溴化条件的影响。 通过在可见光下用三（2,2'-联吡啶基）氯化钌（II）作催化剂的四溴化碳在N，N-二甲基甲酰胺中的处理，将糖半缩醛平稳地转化为相应的糖基溴化物。碳水化合物衍生物中常用的保护基不受温和溴化条件的影响。
• Synthesis of the Repeating Unit of the Capsular Polysaccharide of Streptococcus Pneumoniae Type 3 as a Building Block Suitable for Formation of Oligomers
  作者：Per. Garegg、Stefan Oscarson、Ulf Tedebark

  DOI：10.1080/07328309808002339

  日期：1998.5.1

  The synthesis of a cellobiouronic thioglycoside donor 12, protected with a selectively removable 3′-O-benzyl group is described. The donor 12 is suitable as a monomer building block in the construction of oligomer structures corresponding to the capsular polysaccharide of Streptococcus pneumoniae type 3. The carboxyl function was introduced through regioselective TEMPO-oxidation of a 4′,6′-diol cellobiose

  描述了由可选择性去除的3'- O-苄基保护的纤维二糖硫糖苷供体12的合成。供体12适合作为构建对应于3型肺炎链球菌荚膜多糖的低聚物结构中的单体结构单元。通过对4'，6'-二醇纤维二糖衍生物的区域选择性TEMPO-氧化来引入羧基官能团。如果在2,3,2'，3'，4'，6'-己醇衍生物上进行氧化，则还观察到仲2-羟基和3-羟基的氧化，得到三羧基衍生物作为主要化合物之一产品。硫代糖苷是通过1，6-脱水桥的酸性巯基分解形成的。捐助者12 通过与间隔醇进行糖基化和随后的脱苄基反应，将其转化为合适的起始单体受体。
• Fragmentation pattern of permethyl 6-C-glycosylflavones in electron impact mass spectrometry
  作者：M.L. Bouillant、A. Besset、J. Favre-Bonvin、J. Chopin

  DOI：10.1016/s0031-9422(00)83808-x

  日期：——

  Abstract A mass spectral fragmentation pattern of permethyl 6- C -glycosylflavones is proposed from the MS data of permethyl derivatives mono- O -deuteriomethylated in the 2″-, 3″-, 4″- or 6″-positions. The synthesis of these compounds via O″ -glycosyl-6- C -glucosylflavones is described.

  摘要 根据在 2"-、3"-、4"- 或 6"-位置单-O-氘代甲基化的全甲基衍生物的 MS 数据，提出了全甲基 6-C-糖基黄酮的质谱裂解模式。描述了通过 O''-糖基-6-C-葡萄糖基黄酮合成这些化合物。
• Novel 1,4-benzothiepine 1,1-dioxide derivatives substituted by benzyl radicals, method for their preparation, pharmaceuticals comprising these compounds, and the use thereof
  申请人：Frick Wendelin

  公开号：US20100035961A1

  公开（公告）日：2010-02-11

  This invention relates to Novel 1,4-benzothiepine 1,1-dioxide derivatives substituted by benzyl radicals, method for their preparation, pharmaceuticals comprising these compounds, and the use thereof.

  本发明涉及由苯甲基基团取代的新型1,4-苯硫吩1,1-二氧化物衍生物，其制备方法，包含这些化合物的药物以及它们的用途。