methyl 6-O-(2-azido-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-(2-azido-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: methyl 6-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside；methyl 2,3,4-tri-O-benzyl-6-O-(2-azide-2-deoxy-3,4,6-tri-O-benzyl-D-galactopyranosyl)-α-D-glucopyranoside；methyl 6-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside；(2R,3R,4S,5R,6S)-2-[[(2R,3R,4R,5R,6R)-3-azido-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]-6-methoxy-3,4,5-tris(phenylmethoxy)oxane
• 化学式: C₅₅H₅₉N₃O₁₀
• 分子量: 922.088
• InChiKey: HRKQPNNXEGNRPS-MNMINXCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  68
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3,4,6-三邻苄基半乳醛 在 sodium azide 、 ammonium cerium(IV) nitrate 、 4 A molecular sieve 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 methyl 6-O-(2-azido-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  一类新颖的糖基供体：2-叠氮基-2-脱氧-D-吡喃半乳糖基衍生物的端基S-黄原酸酯

  摘要：

  通过相应半乳糖（1,5-脱水-2-脱氧-D- lyxo）的两步叠氮蒽并化反应，可以轻松制备各种取代的O-乙基S-（2-叠氮基-2-脱氧-D-吡喃半乳糖基）二硫代碳酸酯。（-hex-1-enitols）。它们是有效的糖基供体，用于立体选择性地合成具有生物学重要性的含半乳糖胺的寡糖的保护前体。

  DOI：

  10.1016/s0040-4020(01)87127-1

文献信息

• <i>O</i>-Glycosylation Enabled by <i>N-</i>(Glycosyloxy)acetamides
  作者：Miao Liu、Bo-Han Li、De-Cai Xiong、Xin-Shan Ye

  DOI：10.1021/acs.joc.8b01003

  日期：2018.8.3

  A novel glycosylation protocol has been established by using N-(glycosyloxy)acetamides as glycosyl donors. The N-oxyacetamide leaving group in donors could be rapidly activated in the presence of Cu(OTf)2 or SnCl4 under microwave irradiation. This glycosylation process afforded the coupled products in high yields, and the reaction enjoyed a broad substrate scope, even for disarmed donors and hindered

  通过使用N-（糖基氧基）乙酰胺作为糖基供体已经建立了新的糖基化方案。在微波辐射下，存在Cu（OTf）2或SnCl 4的情况下，供体中的N-氧乙酰胺离去基团可以快速活化。该糖基化过程以高收率提供了偶联产物，并且该反应享有广泛的底物范围，即使对于缴械的供体和受阻的受体也是如此。供体的容易获得，N-（糖基氧基）乙酰胺的高稳定性以及小的离去基团使该方法非常实用。
• Direct Glycosidation of 2‐Azido‐2‐deoxyglycosyl Nitrates
  作者：Yashapal Singh、Tinghua Wang、Alexei V. Demchenko

  DOI：10.1002/ejoc.201900748

  日期：2019.10.9

  Direct glycosylation with 2‐azido nitrate donors has been described. This approach allows to streamline the synthesis of glycans containing amino sugars.

  已经描述了使用2-叠氮基硝酸盐供体的直接糖基化。这种方法可以简化含氨基糖聚糖的合成。
• A highly stereoselective construction of 1,2-trans-β-glycosidic linkages capitalizing on 2-azido-2-deoxy-d-glycosyl diphenyl phosphates as glycosyl donors
  作者：Toshifumi Tsuda、Seiichi Nakamura、Shunichi Hashimoto

  DOI：10.1016/j.tet.2004.08.076

  日期：2004.11

  The scope of TMSOTf-promoted glycosidation of 2-azido-2-deoxyglycopyranosyl diphenyl phosphates is investigated. The 3,4,6-tri-O-benzyl-protected glucosyl and galactosyl donors and the 4,6-O-benzylidene-protected galactosyl donor each react with a range of acceptor alcohols in the presence of a stoichiometric amount of TMSOTf in propionitrile at -78 degreesC to afford 1,2-trans-beta-linked disaccharides in high yields with alpha:beta ratios ranging from 9:91 to 1: > 99, regardless of the anomeric composition of the donor used. The use of propionitrile as a solvent at -78 degreesC has proven to be among the best choice for the highest levels of beta-selectivity reported to date for this type of glycosidation. A plausible reaction mechanism, which features a large equilibrium preference for alpha-glycosyl-nitrilium ions over beta-nitrilium ions, is proposed based on byproducts formed through their intermediacy and accounts for the observed excellent beta-selectivities. (C) 2004 Elsevier Ltd. All rights reserved.
• MARRA, ALBERTO;SHUN, LIAN KIOW SHI;GAUFFENY, FRANSOISE;SINAY, PIERRE, SYNLETT.,(1990) N, C. 445-448
  作者：MARRA, ALBERTO、SHUN, LIAN KIOW SHI、GAUFFENY, FRANSOISE、SINAY, PIERRE

  DOI：——

  日期：——
• A novel class of glycosyl donors: Anomeric S-xanthates of 2-azido-2-deoxy-D-galactopyranosyl derivatives
  作者：Alberto Marra、Françoise Gauffeny、Pierre Sinaÿ

  DOI：10.1016/s0040-4020(01)87127-1

  日期：1991.1

  lactopyranosyl) dithiocarbonates have been easily prepared via a two-step azidoxanthation reaction of the corresponding galactals (1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitols).They are efficient glycosyl donors for the stereoselective synthesis of protected precursors of biologically important galactosamine-containing oligosaccharides.

  通过相应半乳糖（1,5-脱水-2-脱氧-D- lyxo）的两步叠氮蒽并化反应，可以轻松制备各种取代的O-乙基S-（2-叠氮基-2-脱氧-D-吡喃半乳糖基）二硫代碳酸酯。（-hex-1-enitols）。它们是有效的糖基供体，用于立体选择性地合成具有生物学重要性的含半乳糖胺的寡糖的保护前体。