methyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside | 161953-85-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside
• 英文别名: methyl-2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside；[(2R,3R,4S,5S,6R)-2-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 161953-85-1
• 化学式: C₃₀H₃₄O₇
• 分子量: 506.596
• InChiKey: GKWUQQXIMMBMDF-HBMYTODVSA-N

物化性质

• 沸点：
  605.0±55.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside 在 palladium on activated charcoal 4 A molecular sieve 、 四乙基溴化铵 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 228.0h， 生成 methyl α-L-fucopyranosyl-(1->2)-β-D-galactopyranoside
  参考文献：
  名称：

  Oligosaccharides related to xyloglucan: synthesis and X-ray crystal structure of methyl 2-O-(α-?-fucopyranosyl)-β-?-galactopyranoside

  摘要：

  DOI：

  10.1016/0008-6215(96)00030-4
• 作为产物：
  描述：

  2,3,5-三邻苄基-1-o-(4-硝基苯甲酰基)-d-阿拉伯呋喃糖 在 2,2,2-三氯乙醇 、 mercury dibromide 作用下， 以 硝基甲烷 为溶剂， 反应 16.0h， 以87%的产率得到methyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Oligosaccharides related to xyloglucan: synthesis and X-ray crystal structure of methyl 2-O-(α-?-fucopyranosyl)-β-?-galactopyranoside

  摘要：

  DOI：

  10.1016/0008-6215(96)00030-4

文献信息

• Au^III-Halide/Phenylacetylene-Cata­lysed Glycosylations Using 1-<i>O</i>-Acetyl­furanoses and Pyranose 1,2-Ortho­esters as Glycosyl Donors
  作者：Asadulla Mallick、Yakkala Mallikharjunarao、Parasuraman Rajasekaran、Rashmi Roy、Yashwant D. Vankar

  DOI：10.1002/ejoc.201501245

  日期：2016.1

  1-O-Acetylfuranoses and pyranose 1,2-orthoesters were activated with an AuIII halide/phenylacetylene relay catalyst system, and they acted as excellent glycosyl donors. Thus, 1-O-acetyl-D-ribofuranose, 1-O-acetyl-D-lyxofuranose, and 1,2-orthoesters selectively gave the corresponding 1,2-trans glycosides, whereas 1-O-acetyl-D-arabinofuranose and 1-O-acetyl-D-xylofuranose both gave mixtures of 1,2-trans

  1-O-乙酰呋喃糖和吡喃糖 1,2-原酸酯用 AuIII 卤化物/苯乙炔中继催化剂系统活化，它们是优良的糖基供体。因此，1-O-乙酰基-D-呋喃核糖、1-O-乙酰基-D-lyxofuranose 和 1,2-原酸酯选择性地产生相应的 1,2-反式糖苷，而 1-O-乙酰基-D-阿拉伯呋喃糖和1-O-乙酰基-D-呋喃木糖均产生1,2-反式和1,2-顺式糖苷的混合物，其中以1,2-反式糖苷为主。
• Methyltrioxorhenium-Catalyzed Epoxidation-Methanolysis of Glycals under Homogeneous and Heterogeneous Conditions
  作者：Andrea Goti、Francesca Cardona、Gianluca Soldaini、Claudia Crestini、Cinzia Fiani、Raffaele Saladino

  DOI：10.1002/adsc.200505412

  日期：2006.3

  The efficient and high yielding domino epoxidation-methanolysis of glycals 8–15 has been achieved by oxidation with UHP in MeOH catalyzed by MTO. The products have been conveniently isolated as 2-acetoxy derivatives 16–23a, b by direct acetylation of the crude mixtures. Homogeneous MTO-amine complexes 5–7, heterogeneous poly(4-vinylpyridine)/MTO compounds I–III, and microencapsulated polystyrene/MTO

  高效和高产多米诺烯糖的环氧化-甲醇8 - 15已被氧化，UHP在MeOH实现催化由MTO。该产品已被方便地分离为2-乙酰氧基衍生物16 - 23A，B通过将粗混合物直接乙酰化。均质MTO -胺络合物5 - 7，异构聚（4-乙烯基吡啶）/ MTO化合物我- III，和微囊化聚苯乙烯/ MTO系统IV - VII还测试并证明了它们作为氧化步骤催化剂的有效性。取决于基质，氧化的表面非对映选择性从令人满意的到优异的，并且可以通过充分筛选催化剂来优化。在环境友好的实验条件下，使用简单的后处理程序即可获得底物的完全转化和近乎定量的产品收率。
• Partial Benzylation of Methyl α- and β-D-Galactopyranosides
  作者：Naohiko Morishima、Shinkiti Koto、Megumi Oshima、Akiko Sugimoto、Shonosuke Zen

  DOI：10.1246/bcsj.56.2849

  日期：1983.9

  Partial benzylation of methyl α-D-galactopyranoside with benzyl chloride and LiOH selectively gave the 2,3,6-tribenzyl ether, while that using KOH or RbOH gave the 2,4,6-isomer as the main product. Methyl β-D-galactopyranoside afforded the 3,4,6-tribenzyl ether predominantly, irrespective of the alkali used.

  甲基 α-D-吡喃半乳糖苷与苄基氯和 LiOH 选择性地部分苄基化得到 2,3,6-三苄基醚，而使用 KOH 或 RbOH 得到 2,4,6-异构体作为主要产物。无论使用何种碱，甲基 β-D-吡喃半乳糖苷主要提供 3,4,6-三苄基醚。
• The use of selenophenyl galactopyranosides for the synthesis of α and β-(1→4)-C-disaccharides
  作者：Astrid Mallet、Jean-Maurice Mallet、Pierre Sinay

  DOI：10.1016/s0957-4166(00)80403-6

  日期：1994.12

  Methyl alpha-C-lactoside (beta-D-Galp-C-(1-->4)-alpha-D-Glcp-OMe) and its alpha anomer were expeditiously synthesized by radical coupling of various selenophenyl galactopyranosides onto methyl 2,3-di-O -benzyl-4-deoxy-4-C-methylene-alpha-D-xylo-hexopyranoside, which are temporarily connected through a silaketal tether.
• Direct epoxidation of d-glucal and d-galactal derivatives with in situ generated DMDO
  作者：Pavel Cheshev、Alberto Marra、Alessandro Dondoni

  DOI：10.1016/j.carres.2006.09.003

  日期：2006.11

  A multi-gram epoxidation of 3,4,6-tri-O-benzyl-D-glucal and D-galactal with dimethyldioxirane (DMDO) generated in situ from Oxone (R)/acetone in a biphasic system (CH2Cl2-aqueous NaHCO3) resulted in the formation of the corresponding 1,2-anhydrosugars in a 99% yield and 100% selectivity. In a similar way, 3,4,6-tri-O-acetyl-D-glucal afforded a 7:1 mixture of the corresponding gluco and manno derivatives in an 87% overall yield. (c) 2006 Elsevier Ltd. All rights reserved.