methyl 2,3-di-O-benzyl-6-O-benzoyl-β-D-galactopyranoside | 20786-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-6-O-benzoyl-β-D-galactopyranoside
• 英文别名: methyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranoside；Methyl-6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosid；[(2R,3S,4S,5R,6R)-3-hydroxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methyl benzoate
• CAS: 20786-72-5
• 化学式: C₂₈H₃₀O₇
• 分子量: 478.542
• InChiKey: GAFQPRARNIDGOF-BZTMQRDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  methyl 2,3-di-O-benzyl-6-O-benzoyl-β-D-galactopyranoside 在 吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 四丁基溴化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 41.5h， 生成
  参考文献：
  名称：

  Vinyl bis-sulfone methodology in thiosugars: selective access to chiral thiovinyl sulfones and PSE oxathianes

  摘要：

  Based on the vinyl biS-sulfone methodology previously developed to synthesize PSE acetals, an original approach to homochiral carbohydrate-derived PSE 1,3-oxathianes is described. The ready formation of intermediate phenylsul fonyl vinyl sulfides, which have a synthetic potential of their own, emphasizes the versatility of the method. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.023
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 盐酸 、 甲醇 、 sodium hydroxide 、 四丁基高氯酸铵 、 sodium hydride 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2,3-di-O-benzyl-6-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of rhamnogalacturonan I oligosaccharides: synthesis of a tetrasaccharide intermediate

  摘要：

  A hydroxyl protected tetrasaccharide intermediate, corresponding to a segment of the rhamnogalacturonan I polysaccharide, has been synthesized using the glycosyl imidate technique. This tetrasaccharide is designed to allow for further elongation and branching. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00494-7

文献信息

• Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase
  作者：Yuchao Lu、Chenxi Hou、Jingli Ren、Xiaoting Xin、Hengfu Xu、Yuxin Pei、Hai Dong、Zhichao Pei

  DOI：10.3390/molecules21050641

  日期：——

  A novel metal-free organobase-catalyzed regioselective benzoylation of diols and carbohydrates has been developed. Treatment of diol and carbohydrate substrates with 1.1 equiv. of 1-benzoylimidazole and 0.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in MeCN under mild conditions resulted in highly regioselective benzoylation for the primary hydroxyl group. Importantly, compared to most commonly

  已经开发出一种新型的无金属有机碱催化的二醇和碳水化合物的区域选择性苯甲酰化。用 1.1 当量处理二醇和碳水化合物底物。1-苯甲酰咪唑和 0.2 当量。1,8-二氮杂双环[5.4.0] undec-7-ene (DBU) 在温和条件下在 MeCN 中的反应导致伯羟基的高度区域选择性苯甲酰化。重要的是，与最常用的伯羟基保护基团相比，苯甲酰基保护基团提供了一种新的保护策略。
• Stannous chloride as a low toxicity and extremely cheap catalyst for regio-/site-selective acylation with unusually broad substrate scope
  作者：Jian Lv、Jian-Cheng Yu、Guang-Jing Feng、Tao Luo、Hai Dong

  DOI：10.1039/d0gc02739a

  日期：——

  containing cis-vicinal diol, the substrate scope also includes glycosides without cis-vicinal diol. For such a substrate scope, usually, only methods using stoichiometric amounts of organotin reagents can lead to the same protection pattern with high selectivities and highly isolated yields (84–97% in most cases). Therefore, SnCl2, as a low toxicity and extremely cheap reagent, should be the best catalyst

  这项工作报告了氯化亚锡（SnCl 2）催化的区域/位点选择性酰化反应，其底物范围异常广泛。除了含有顺式-邻位二醇的1,2-和1,3-二醇和糖苷外，底物范围还包括不含顺式-邻位二醇的糖苷。对于这种底物范围，通常，只有使用化学计量的有机锡试剂的方法才能以高选择性和高分离产率（大多数情况下为84–97％）产生相同的保护模式。因此，与以前报道的任何试剂相比，SnCl 2作为一种低毒且极其便宜的试剂，应该是区域/位点选择性酰化反应的最佳催化剂。
• Synthesis of methyl 4-thio-β-cellobioside. A reinvestigation
  作者：Vincent Moreau、Jens Chr. Norrild、Hugues Driguez

  DOI：10.1016/s0008-6215(97)00046-3

  日期：1997.5

  Abstract The best yield for the synthesis of the title compound was obtained by nucleophilic displacement of the 4- O -triflyl group in methyl tri -O- benzyl -4-O- triflyl -β- d - galactopyranoside by 2,3,4,6- tetra -O- acetyl -1-S- acetyl-1-thio -β- d - glucopyranose in HMPA in the presence of diethylamine. Under these conditions, the formation of unsaturated side products was decreased.

  摘要通过亲核置换甲基三-O-苄基-4-O-三flyl-β-d-半乳糖吡喃糖苷中的4-O-三氟甲苯基，可得到2,3,4的最佳收率。在二乙胺存在下，HMPA中的6-四-O-乙酰基-1-S-乙酰基-1-硫代-β-d-吡喃葡萄糖。在这些条件下，减少了不饱和副产物的形成。
• DBN-Catalyzed Regioselective Acylation of Carbohydrates and Diols in Ethyl Acetate
  作者：Bo Ren、Mengyao Zhang、Shijie Xu、Lu Gan、Li Zhang、Lin Tang

  DOI：10.1002/ejoc.201900776

  日期：2019.8.7

  The 1,5‐diazabicyclo[4.3.0]non‐5‐ene (DBN)‐catalyzed, highly efficient and relatively green regioselective acylation of carbohydrates and diols is firstly developed. The hydroxyl groups can be selectively acylated by the corresponding anhydride in EtOAc in the presence of a catalytic amount (as low as 0.1 equiv.) of DBN at room temperature to 40 °C.

  碳水化合物和二醇的1,5-二氮杂双环[4.3.0] non-5-ene（DBN）催化，高效且相对绿色的区域选择性酰化反应是最先开发的。在室温至40°C下，在存在催化量（低至0.1当量）的DBN的情况下，可用相应的酸酐在EtOAc中将羟基选择性地酰化。
• Observations on Iodine-promoted β-Mannosylation
  作者：Robert Field、Steven Marsh、K. Kartha

  DOI：10.1055/s-2003-40346

  日期：——

  The stereoselectivity of iodine-promoted glycosylation with mannosyl sulfoxides gives rise to unexpected β-selectivity with less reactive alcohol acceptors. Less reactive accceptors also give better coupling yields. Comparison of iodine with other promoters highlights differences in reaction rates and stereoselectivities indicative of different reaction mechanisms.

  碘促进的甘露糖苷化反应中，甘露糖磺氧化物的立体选择性导致在反应活性较低的醇受体中出现意外的β-选择性。反应活性较低的受体也产生更好的耦合产率。将碘与其他促进剂进行比较，突显了反应速率和立体选择性方面的差异，表明了不同的反应机制。