(2R,3R,4S,5S,6R)-4-氨基-2-[(2S,3R,4S,5S,6R)-4-氨基-3,5-二羟基-6-(羟基甲基)四氢吡喃-2-基]氧基-6-(羟基甲基)四氢吡喃-3,5-二醇 | 104196-14-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2R,3R,4S,5S,6R)-4-氨基-2-[(2S,3R,4S,5S,6R)-4-氨基-3,5-二羟基-6-(羟基甲基)四氢吡喃-2-基]氧基-6-(羟基甲基)四氢吡喃-3,5-二醇
• 英文名称: 3-amino-3-deoxy-a-D-glucopyranosyl-(1→1')-3'-amino-3'-deoxy-b-D-glucopyranoside
• 英文别名: neotrehalosyl 3,3'-diamine；NTD；BMY-28251；3,3'-Neotrehalosadiamine；(2S,3R,4S,5S,6R)-4-amino-2-[(2R,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-3,5-diol
• CAS: 104196-14-7
• 化学式: C₁₂H₂₄N₂O₉
• 分子量: 340.331
• InChiKey: ZPEFXARQZVAHGO-DCSYEGIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  201
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  在 甲醇 、 氢气 、 sodium 、 palladium(II) hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 (2R,3R,4S,5S,6R)-4-氨基-2-[(2S,3R,4S,5S,6R)-4-氨基-3,5-二羟基-6-(羟基甲基)四氢吡喃-2-基]氧基-6-(羟基甲基)四氢吡喃-3,5-二醇
  参考文献：
  名称：

  天然海藻糖胺和合成的1,1'-二糖氨基糖苷的多元合成

  摘要：

  简短而甜美：合成了十种二糖氨基糖苷的通用策略，其中包括三种天然海藻糖胺，新海藻糖基3,3'-二胺和六种合成氨基糖苷。氨基糖苷化合物具有不同的端基构型和氨基数。立体定向供体与构型稳定的TMS糖苷受体的糖基化偶联是关键步骤。

  DOI：

  10.1002/cbic.201800656

文献信息

• Processes and host cells for genome, pathway, and biomolecular engineering
  申请人：enEvolv, Inc.

  公开号：US10370654B2

  公开（公告）日：2019-08-06

  The present disclosure provides compositions and methods for genomic engineering.

  本公开提供了基因组工程的组合物和方法。
• Synthesis of 3,3′-neotrehalosadiamine and related 1,1′-aminodisaccharides using disarmed, armed, and superarmed building blocks
  作者：Shazia Anjum、Natasha D. Vetter、Joseph E. Rubin、David R.J. Palmer

  DOI：10.1016/j.tet.2012.10.058

  日期：2013.1

  Here we report a high yielding, stereoselective synthesis of the naturally occurring 1,1'-disaccharide neotrehalosadiamine (NTD) and some related analogs. Following an eleven-step sequence, seven of which did not require chromatographic separation, NTD was generated in 60% overall yield from the inexpensive, commercially available precursor 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose. The key alpha,beta-linkage of NTD was formed in a highly stereoselective manner by taking advantage of the participating effect of the acyl group at O-2 of the donor glycoside. The influence of electronic effects of disarmed, armed, and superarmed glycosyl donors and acceptors on the outcome of 1,1'-glycosidation was also observed. Antibacterial studies using NTD and its analogs show detectable but weak antistaphylococcal activity. (c) 2012 Elsevier Ltd. All rights reserved.
• PROCESSES AND HOST CELLS FOR GENOME, PATHWAY, AND BIOMOLECULAR ENGINEERING
  申请人：ENEVOLV, INC.

  公开号：US20160186168A1

  公开（公告）日：2016-06-30

  The present disclosure provides compositions and methods for genomic engineering.
• US9944925B2
  申请人：——

  公开号：US9944925B2

  公开（公告）日：2018-04-17
• Diverse Synthesis of Natural Trehalosamines and Synthetic 1,1′-Disaccharide Aminoglycosides
  作者：Yen-Chu Lu、Soumik Mondal、Ching-Chi Wang、Chun-Hung Lin、Kwok-Kong Tony Mong

  DOI：10.1002/cbic.201800656

  日期：2019.1.18

  Short and sweet: A general strategy for the synthesis of ten disaccharide aminoglycosides, including three natural trehalosamines, neotrehalosyl 3,3′‐diamine, and six synthetic aminoglycosides, is developed. The aminoglycoside compounds have different anomeric configurations and numbers of amino groups. Glycosylation coupling of a stereodirecting donor with a configuration‐stable TMS glycoside acceptor

  简短而甜美：合成了十种二糖氨基糖苷的通用策略，其中包括三种天然海藻糖胺，新海藻糖基3,3'-二胺和六种合成氨基糖苷。氨基糖苷化合物具有不同的端基构型和氨基数。立体定向供体与构型稳定的TMS糖苷受体的糖基化偶联是关键步骤。