methyl 6-O-(2-azido-tri-O-benzyl-2-deoxy-α-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-α-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-α-D-galactopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside；methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1→6)-2,3,4-tri-O-benzyl-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-[[(2S,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-VYFLKZLASA-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-α-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

• A flexible 1,2-cis α-glycosylation strategy based on in situ adduct transformation
  作者：Jhe-Cyuan Hu、Ai-Fen Wendy Feng、Bo-Yao Chang、Chun-Hung Lin、Kwok-Kong Tony Mong

  DOI：10.1039/c7ob00839b

  日期：——

  strategy for a wide range of glycosyl donors and acceptors has been developed, which is based on an in situ adduct transformation protocol. Based on this strategy, both NFM-derived and iodide covalent adducts can be accessed for glycosylation. Using low temperature NMR spectroscopy, the aforementioned glycosyl adducts were detected.

  已经开发了一种针对多种糖基供体和受体的灵活的1,2-顺式α-选择性糖基化策略，该策略基于原位加合物转化方案。基于此策略，可以获取NFM衍生品和碘化物共价加合物进行糖基化。使用低温NMR光谱法，检测到上述糖基加合物。
• 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：——