Methyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside | 162552-79-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside
• 英文别名: (2R,3S,4R,5R,6S)-5-azido-6-methoxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 162552-79-6
• 化学式: C₂₁H₂₅N₃O₅
• 分子量: 399.447
• InChiKey: VZMHLEUVUOIBDE-ONUIULTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 在 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 palladium 10% on activated carbon 、 氢氟酸 、 氢气 、 双氧水 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 74.5h， 生成
  参考文献：
  名称：

  Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides

  摘要：

  The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag. attached at the reducing end is reported. The fluorous tert-butyl dicarbonate ((F)Boc) tag did not interfere with enzymatic recognition for both elongation and specific sulfation, and flash purification was performed by standard fluorous solid-phase extraction (FSPE). Based on an (F)Boc attached disaccharide as acceptor, a series of partial N-sulfated, 6-O-sulfated heparan sulfate. oligosaccharides were successfully synthesized employing fluorous techniques.

  DOI：

  10.1021/ol500738g
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 吡啶 、 三乙基硅烷 、 4-二甲氨基吡啶 、 sodium azide 、 三氟甲磺酸酐 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 copper(II) sulfate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 74.5h， 生成 Methyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides

  摘要：

  The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag. attached at the reducing end is reported. The fluorous tert-butyl dicarbonate ((F)Boc) tag did not interfere with enzymatic recognition for both elongation and specific sulfation, and flash purification was performed by standard fluorous solid-phase extraction (FSPE). Based on an (F)Boc attached disaccharide as acceptor, a series of partial N-sulfated, 6-O-sulfated heparan sulfate. oligosaccharides were successfully synthesized employing fluorous techniques.

  DOI：

  10.1021/ol500738g

文献信息

• Stereoselective Iterative One-Pot Synthesis of <i>N</i>-Glycolylneuraminic Acid-Containing Oligosaccharides
  作者：David Crich、Baolin Wu

  DOI：10.1021/ol801548k

  日期：2008.9.18

  The use of an N-acyloxazolidinone-protected S-adamantanyl thiosialoside allows the highly stereoselective, one-pot multicomponent synthesis of alpha-sialoside-based oligosaccharides.

  使用 N-酰基恶唑烷酮保护的 S-金刚烷基硫代唾液酸允许高度立体选择性、一锅多组分合成基于 α-唾液酸苷的寡糖。
• Metal Trifluoromethanesulfonate-Catalyzed Regioselective Reductive Ring Opening of Benzylidene Acetals
  作者：Chi-Rung Shie、Zheng-Hao Tzeng、Cheng-Chung Wang、Shang-Cheng Hung

  DOI：10.1002/jccs.200900076

  日期：2009.6

  study of various metal trifluoromethanesulfonates as efficient catalysts in the regioselective reductive ring opening of benzylidene acetals is described, including the effects of solvents, reducing agents, and temperature. These catalysts are found to be effective in cleaving the 4,6‐O‐acetal rings of hexopyranosides at either O4 or O6, respectively. When used in conjunction with a 1 M solution of

  系统地研究了各种金属三氟甲磺酸盐作为亚苄基乙缩醛的区域选择性还原开环中的有效催化剂，包括溶剂，还原剂和温度的影响。发现这些催化剂可有效裂解六吡喃糖苷在O4或O6处的4,6- O-乙缩醛环。与1M BH 3溶液一起使用时·THF中的THF无需额外添加任何溶剂，它会影响O6位置的环裂变以生成相应的伯醇，而在乙腈中以二甲基乙基硅烷作为还原剂存在会导致O4的开环，从而导致生成仲羟基衍生物高选择性和高收率。这些方法可以应用于包含各种官能团的多种基材。
• The 4-(<i>tert</i>-Butyldiphenylsiloxy)-3-fluorobenzyl Group: A New Alcohol Protecting Group, Fully Orthogonal with the <i>p</i>-Methoxybenzyl Group and Removable under Desilylation Conditions
  作者：David Crich、Linfeng Li、Michio Shirai

  DOI：10.1021/jo900026e

  日期：2009.3.20

  ether-type protecting group for alcohols, the 4-(tert-butyldiphenylsiloxy)-3-fluorobenzyl group, is introduced. The protecting group is introduced by means of the readily prepared benzyl bromide and is cleaved with tetrabutylammonium fluoride in dimethylformamide under microwave irradiation. The fluoride substituent provides stability to oxidizing conditions, such that the new protecting group is fully

  引入了一种新的苄基醚型醇保护基团，4-(叔丁基二苯基硅氧基)-3-氟苄基。保护基通过容易制备的苄基溴引入，并在微波辐射下用四丁基氟化铵在二甲基甲酰胺中裂解。氟化物取代基提供了对氧化条件的稳定性，使得新的保护基团与用DDQ去除对甲氧基苄基醚完全相容。介绍了新的保护基团在直接立体控制合成β-吡喃甘露糖苷中的应用。
• Production Of L-Iduronate Containing Polysaccharides
  申请人：Hansen Steen Uldall

  公开号：US20100317846A1

  公开（公告）日：2010-12-16

  A process for the production of polysaccharide (20) from disaccharide (10) and saccharide (21), wherein R 1 to R 10 are each independently the same or different protecting groups; R is an optionally substituted aryl group or an optionally substituted saturated or unsaturated alkyl group; X is selected from the group consisting of hydrogen, alkyl and amino; Y is selected from the group consisting of a protecting group and one or more saccharide residues; and n is a positive integer; and further wherein said process comprises removal of the R 7 protecting group and reaction of the deprotected C4-oxygen atom of compound (21) with the C1-carbon atom of the 1-ido moiety of compound (10).

  从二糖（10）和糖（21）中生产多糖（20）的工艺，其中R1至R10分别是相同或不同的保护基；R是可选的取代芳基或可选的饱和或不饱和烷基；X选自氢，烷基和氨基等组；Y选自保护基和一个或多个糖基残基；n是正整数；并且进一步包括去除R7保护基和使化合物（21）的去保护的C4氧原子与化合物（10）的1-碘基团的C1碳原子反应的步骤。
• One-Pot Synthesis of<i>N</i>-Acetyl- and<i>N</i>-Glycolylneuraminic Acid Capped Trisaccharides and Evaluation of Their Influenza A(H1 N1) Inhibition
  作者：Yun Hsu、Hsiu-Hwa Ma、Larry S. Lico、Jia-Tsrong Jan、Koichi Fukase、Yosuke Uchinashi、Medel Manuel L. Zulueta、Shang-Cheng Hung

  DOI：10.1002/anie.201309646

  日期：2014.2.24

  N‐acetylneuraminic acid (Neu5Ac) α(2→6)‐linked to galactose (Gal) as binding sites for influenza virus hemagglutinin. N‐Glycolylneuraminic acid (Neu5Gc) in place of Neu5Ac is known to affect hemagglutinin binding in other species. Not normally generated by humans, Neu5Gc may find its way to human cells from dietary sources. To compare their influence in influenza virus infection, six trisaccharides with Neu5Ac

  人肺上皮细胞天然地提供与半乳糖（Gal）连接的末端N-乙酰神经氨酸（Neu5Ac）α（2→6）-作为流感病毒血凝素的结合位点。已知用N-乙二醇神经氨酸（Neu5Gc）替代Neu5Ac会影响其他物种中的血凝素结合。Neu5Gc通常不是人类产生的，它可能会通过饮食来源找到进入人体细胞的途径。为了比较它们对流感病毒感染的影响，使用一锅装配和发散转化制备了六种带有与Gal相连的Neu5Ac或Neu5Gcα（2→6）和不同还原糖单位的三糖。糖组件使用N邻苯二甲酰基保护的亚氨基唾液酸亚胺酸酯，可与硫代半乳糖苷进行化学选择性活化和α-立体选择性偶联。对细胞病变作用的评估表明，Neu5Gc封端的三糖对病毒感染的抑制作用优于其Neu5Ac对应物。