甲基2-O-苯甲酰基-4,6-O-亚苄基-beta-D-吡喃葡萄糖苷 | 38992-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 中文名称: 甲基2-O-苯甲酰基-4,6-O-亚苄基-beta-D-吡喃葡萄糖苷
• 英文名称: methyl 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside
• 英文别名: methyl 4,6-O-benzylidene-2-O-benzoyl-β-D-glucopyranoside；Methyl-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranoside；[(4aR,6R,7R,8S,8aS)-8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzoate
• CAS: 38992-99-3
• 化学式: C₂₁H₂₂O₇
• 分子量: 386.401
• InChiKey: WHKUKOCUXSRSAR-LTFOGXKFSA-N

物化性质

• 沸点：
  561.7±50.0 °C(Predicted)
• 密度：
  1.34±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：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲基2-O-苯甲酰基-4,6-O-亚苄基-beta-D-吡喃葡萄糖苷 在 2,6-二甲基吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 硫脲 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 Methyl O-(2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the laminara-oligosaccharide methyl β-glycosides of dp 3–8

  摘要：

  Ethyl 2,3,4,6-tetra-O-acetyl-l-thio-alpha-D-glucopyranoside has been prepared in a good yield by anomerization of the corresponding beta-thioglucoside with tin(IV) chloride and transformed, in three steps, into ethyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-alpha-D-glucopyranoside (18). Chloroacetylation of 18, followed by treatment of the product with chlorine gave crystalline 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-beta-D-glucopyranosyl chloride (20). This was coupled with methanol in the presence of silver carbonate-silver perchlorate and the product was O-dechloroacetylated to afford methyl 2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranoside (22). Silver triflate-promoted glucosylation of 18 with 20 gave a beta-(1 --> 3)-linked disaccharide derivative, reaction of which with chlorine yielded crystalline O-(2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-beta-D-glucopyranosyl)-(1 --> 3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl chloride (24). Likewise, condensation of 22 with 20 gave a beta-(1 --> 3)-linked disaccharide glycoside, which was partially deprotected to give methyl O-(2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-(1 --> 3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranoside (26). The methyl beta-glycosides of a homologous series of (1 --> 3)-linked beta-D-gluco-Oligosaccharides from the tri- to the octa-saccharide have been synthesized in a blockwise manner by using 22 and 26 as the glycosyl acceptors, 24 as the disaccharide donor, and silver triflate as the promoter.

  DOI：

  10.1016/0008-6215(93)80061-i
• 作为产物：
  描述：

  Ethyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-glucopyranoside 在 吡啶 、 2,6-二甲基吡啶 、 4 A molecular sieve 、 silver perchlorate 、 氯 、 硫脲 、 silver carbonate 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 氯仿 为溶剂， 反应 6.41h， 生成 甲基2-O-苯甲酰基-4,6-O-亚苄基-beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Synthesis of the laminara-oligosaccharide methyl β-glycosides of dp 3–8

  摘要：

  Ethyl 2,3,4,6-tetra-O-acetyl-l-thio-alpha-D-glucopyranoside has been prepared in a good yield by anomerization of the corresponding beta-thioglucoside with tin(IV) chloride and transformed, in three steps, into ethyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-alpha-D-glucopyranoside (18). Chloroacetylation of 18, followed by treatment of the product with chlorine gave crystalline 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-beta-D-glucopyranosyl chloride (20). This was coupled with methanol in the presence of silver carbonate-silver perchlorate and the product was O-dechloroacetylated to afford methyl 2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranoside (22). Silver triflate-promoted glucosylation of 18 with 20 gave a beta-(1 --> 3)-linked disaccharide derivative, reaction of which with chlorine yielded crystalline O-(2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-beta-D-glucopyranosyl)-(1 --> 3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl chloride (24). Likewise, condensation of 22 with 20 gave a beta-(1 --> 3)-linked disaccharide glycoside, which was partially deprotected to give methyl O-(2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-(1 --> 3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranoside (26). The methyl beta-glycosides of a homologous series of (1 --> 3)-linked beta-D-gluco-Oligosaccharides from the tri- to the octa-saccharide have been synthesized in a blockwise manner by using 22 and 26 as the glycosyl acceptors, 24 as the disaccharide donor, and silver triflate as the promoter.

  DOI：

  10.1016/0008-6215(93)80061-i

文献信息

• Regioselective O-deacylation of fully acylated glycosides and 1,2-O-isopropylidenealdofuranose derivatives with hydrazine hydrate
  作者：Hoshiharu Ishido、Nobuo Sakairi、Masao Sekiya、Nobuo Nakazaki

  DOI：10.1016/s0008-6215(00)80525-x

  日期：1981.11

  partial O -deacylation of fully acylated methyl glycosides and some other glycosyl compounds (23 compounds) was found to be induced, to give, in good yields, products bearing one free hydroxyl group; the results obtained indicated that, among the primary and secondary O -acyl groups, the 2- O -acyl groups were, in general, the most labile toward the nucleophile (hydrazine). Hydrazinolysis of 1,2- O -

  摘要在1：4乙酸-吡啶中进行肼解后，在吡啶中，可诱导完全酰化的甲基糖苷和某些其他糖基化合物（23种化合物）的部分O-脱酰作用，从而以较高的收率得到含1种化合物的产物。游离羟基 所得结果表明，在伯和仲O-酰基中，2-O-酰基通常对亲核试剂（肼）最不稳定。另一方面，对1，2-O-异亚丙基戊二醛呋喃糖酰化物（3种化合物）进行水合肼解，以高收率得到相应的在其伯羟基上具有保护基的单酰基衍生物。讨论了可能与肼解的区域选择性有关的因素。
• Regioselective Acylation of Carbohydrates with 1-Acyloxy-1<i>H</i>-benzotriazoles
  作者：István F. Pelyvás、Thisbe K. Lindhorst、Harald Streicher、Joachim Thiem

  DOI：10.1055/s-1991-26635

  日期：——

  Acylation of representative carbohydrate derivatives was accomplished with in situ generated 1-acyloxy-1H-benzotriazoles. The observed high regioselectivity, mild reaction conditions and convenient work-up make the presented one-pot procedure generally applicable and more advantageous than acylations with previously introduced reagents, including N-acylimidazoles.

  代表性碳水化合物衍生物的酰化反应是通过原位生成的1-酰氧基-1H-苯并三唑完成的。所观察到的较高的位选择性、温和的反应条件和简便的后续处理使得所提出的单锅法具有普遍适用性，并且比之前引入的试剂（包括N-酰基咪唑）的酰化反应更具优势。
• Silver(I) Oxide Mediated Selective Monoprotection of Diols in Pyranosides
  作者：Haisheng Wang、Ji She、Li-He Zhang、Xin-Shan Ye

  DOI：10.1021/jo0497252

  日期：2004.8.1

  The reaction of 4, 6-O-benzylidene-d-pyranosides with a stoichiometric amount of TsCl, AcCl, and BzCl in the presence of silver(I) oxide and a catalytic amount of potassium iodide led to monosubstituted derivatives in high regioselectivity and in good yields.

  的4反应，6- ö -benzylidene- d -pyranosides用的TsCl，ACCL，和BzCl的在银存在的化学计量量（I），氧化，并导致高的区域选择性和在单取代的衍生物碘化钾催化量良品率高。
• Selective benzoylation of diols with 1-(benzoyloxy)benzotriazole
  作者：Sunggak Kim、Heung Chang、Wan Ju Kim

  DOI：10.1021/jo00210a036

  日期：1985.5
• Regioselective alkylation, benzoylation, and p-toluenesulfonylation of methyl 4,6-O-benzylidene-β-d-glucopyranoside
  作者：Ken'ichi Takeo、Kazuko Shibata

  DOI：10.1016/0008-6215(84)85190-3

  日期：1984.10