2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose
• 英文别名: 1-formyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside；(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane-2-carbaldehyde
• 化学式: C₃₅H₃₆O₆
• 分子量: 552.667
• InChiKey: KKPOREZWWWRARY-IVFJIKSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose 在 喹啉 、 palladium, 5% on calcium carbonate, poisoned with lead 氢气 、 potassium carbonate 、 magnesium bromide 作用下， 以 甲醇 、 乙醚 、 乙酸乙酯 为溶剂， 生成 1-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]prop-2-en-1-ol
  参考文献：
  名称：

  A Pd(0)-catalyzed route to functionalized β-C-glycosides from β-C-glycosylaldehydes

  摘要：

  C-glycosides are synthesized in five steps starting from beta-C-glycosylaldehydes 1 and 2. The key step is a Pd(0)-catalyzed alkylation that leads regio and stereoselectively to exotic compounds by formation of C-C and C-N bonds. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10067-3
• 作为产物：
  描述：

  2-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)thiazole 在 sodium tetrahydroborate 、 三氟甲烷磺酸甲酯 、 mercury dichloride 作用下， 生成 2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose
  参考文献：
  名称：

  Thiazole-based synthesis of C-glycosyl aldehydes

  摘要：

  The formylation at the anomeric carbon of the model sugars 2,3,4,6-tetra-O-benzyl-D-glucopyranose and 2,3:5,6-di-O-isopropylidene-D-mannofuranose is carried out by addition of 2-lithiothiazole to the corresponding lactones followed by reductive dehydroxylation and thiazole to formyl deblocking.

  DOI：

  10.1016/s0040-4039(00)79319-1

文献信息

• Synthesis of Benzyl <i>C</i> -Analogues of Dapagliflozin as Potential SGLT2 Inhibitors
  作者：Ramesh Mukkamala、Roshan Kumar、Sanjay K. Banerjee、Indrapal Singh Aidhen

  DOI：10.1002/ejoc.202000025

  日期：2020.3.31

  A convenient synthetic strategy has been developed for the synthesis of C‐benzyl analogues of dapagliflozin. The In vitro sodium‐glucose co‐transporters (SGLT1 and SGLT2) inhibition activity of all new compounds exhibits promising results, particularly, compound 14 emerged as the most potent SGLT2 inhibitor with the best selectivity for inhibition of SGLT2 (IC50:0.64 nm) over SGLT1 (IC50: 500 nm) as

  已经开发了一种方便的合成策略，用于合成达格列净的C-苄基类似物。所有新化合物的体外葡萄糖钠共转运蛋白（SGLT1和SGLT2）抑制活性均显示出令人鼓舞的结果，特别是化合物14以最强的SGLT2抑制剂的形式出现，对SGLT2的抑制作用具有最佳选择性（IC 50：0.64 n m）相比于Dapagliflozin （SGLT1）（IC 50：500 n m）。
• Design and Use of an Oxazolidine Silyl Enol Ether as a New Homoalanine Carbanion Equivalent for the Synthesis of Carbon-Linked Isosteres of <i>O</i>-Glycosyl Serine and <i>N</i>-Glycosyl Asparagine
  作者：Alessandro Dondoni、Alberto Marra、Alessandro Massi

  DOI：10.1021/jo981861h

  日期：1999.2.1

  A trimethylsilyl enol ether carrying the N-Boc 2,2-dimethyloxazolidine ring was designed to serve as a synthetic equivalent of the homoalanine carbanion for the introduction of the alpha-amino acid side chain at the anomeric carbon of sugars. This new functionalized silyl enol ether was prepared in multigram scale and high enantiomeric purity starting from methyl N-Boc-L-threoninate (six steps, 49%

  设计带有N-Boc 2，2-二甲基恶唑烷环的三甲基甲硅烷基烯醇醚，作为高丙氨酸碳负离子的合成等同物，用于在糖的异头碳处引入α-氨基酸侧链。从N-Boc-L-苏氨酸甲酯开始，以克级数和高对映体纯度制备这种新的官能化甲硅烷基烯醇醚（六步，收率49％）。该试剂用于C-糖基氨基酸的两种合成方法。在一种方法中，由BF（3）.Et（2）O促进的与四-O-苄基-D-吡喃半乳糖基三氯乙酰亚胺酸酯的偶联提供了作为主要产物的α-连接的C-糖苷（分离出的收率为30％）用叔丁基锂转化为β-连接的异构体。通过Barton-McCombie方法对这些化合物进行脱氧，并通过琼斯试剂的氧化裂解从恶唑烷环上脱除糖基部分，从而得到C-糖基丝氨酸等位基因α-和β-Gal-CH（2）（）-Ser。以类似的方式从四-O-苄基-D-吡喃葡萄糖基三氯乙酰亚胺酸酯开始制备α-和β-Glc-CH（2）（）-Ser。在第二种方法中，在BF（
• Multigram scale synthesis of formyl tetra-O-benzyl-β-d-C-glucopyranoside using benzothiazole as a formyl group equivalent
  作者：Alessandro Dondoni、Alberto Marra

  DOI：10.1016/s0040-4039(02)02525-x

  日期：2003.1

  β-d-glucopyranoside; treatment of this mixture with sodium methoxide gives the β-anomer from which the title aldehyde is obtained in a pure form by transformation of the benzothiazole ring into the formyl group.

  向d-葡糖酸内酯中加入2-硫代苯并噻唑，然后将所得酮糖脱氧，得到苯并噻唑基α-和β-d-吡喃葡萄糖苷的混合物。用甲醇钠处理该混合物得到β-异头物，通过将苯并噻唑环转化成甲酰基，以纯净形式得到标题醛。
• Convenient Access to 2-β-<scp>d</scp>-Glucopyranosylpyridines by Using Bohlmann-Rahtz Heteroannulation
  作者：Mannem Rajeswara Reddy、Indrapal Singh Aidhen

  DOI：10.1002/ejoc.201800789

  日期：2018.11.8

  A Bohlmann–Rahtz heteroannulation between a sugar alkynone and ethyl β‐aminocrotonate gives 2‐β‐d‐Glucopyranosylpyridines. 10 examples were prepared based on the importance of varying the aglycon part of Dapagliflozin. The synthesized compounds were envisaged as potential analogues of Dapagliflozin.

  糖炔酮和β-氨基巴豆酸乙酯之间的Bohlmann-Rahtz杂环化产生2-β- d-葡萄糖基核糖基吡啶。基于改变达格列净的糖苷配基部分的重要性，制备了10个实施例。设想合成的化合物为达格列净的潜在类似物。
• Convenient Synthesis of 3-Glycosylated Isocoumarins
  作者：Kasireddy Sudarshan、Indrapal Singh Aidhen

  DOI：10.1002/ejoc.201601264

  日期：2017.1.3

  A new route for the synthesis of 3-substituted and 8-hydroxy-3-substituted isocoumarins has been developed by using modified Julia olefination for initial C-C bond formation between aldehydes and benzylic-sulfones. Palladium-catalyzed Meinwald rearrangement was used as a key step for the obtainment of ketone intermediates, which on base promoted intramolecular cyclization afforded the desired isocoumarins

  通过使用改良的 Julia 烯化在醛和苄基砜之间形成初始 CC 键，开发了一种合成 3-取代和 8-羟基-3-取代异香豆素的新途径。钯催化的 Meinwald 重排被用作获得酮中间体的关键步骤，其在基础上促进了分子内环化，得到了所需的异香豆素。所开发的方法首次为迄今为止未知的 3- 糖基异香豆素和特别是其中葡糖基部分连接到异香豆素骨架的吡喃酮环的 3- 糖基异香豆素铺平了道路。