6,6'-diazido-2,3,2',3'-tetra-O-benzyl-6,6'-dideoxy-α,α-trehalose | 99697-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6'-diazido-2,3,2',3'-tetra-O-benzyl-6,6'-dideoxy-α,α-trehalose
• 英文别名: 2,2',3,3'-tetra-O-benzyl-6,6'-diazido-6,6'-dideoxy-α-D-trehalose；(2R,3R,4S,5R,6R)-2-(azidomethyl)-6-[(2R,3R,4S,5R,6R)-6-(azidomethyl)-5-hydroxy-3,4-bis(phenylmethoxy)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 99697-39-9
• 化学式: C₄₀H₄₄N₆O₉
• 分子量: 752.824
• InChiKey: VDJKWBPWCYWYJJ-AELZGUPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  55
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  6,6'-diazido-2,3,2',3'-tetra-O-benzyl-6,6'-dideoxy-α,α-trehalose 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以75%的产率得到6,6'-diamino-2,3,2',3'-tetra-O-benzyl-6,6'-dideoxy-α,α-trehalose
  参考文献：
  名称：

  Lethal and adjuvant activities of cord factor (trehalose-6,6'-dimycolate) and synthetic analogs in mice.

  摘要：

  分枝杆菌糖脂，曲哈洛糖-6，6'-二甲氧基酸酯（TDM）及其类似物，6，6'-二-O-三碳酰基-α，α-曲哈洛糖[TD (L30)]，6，6'-双-O-(2-十四烷基十六烷酰基)-α、6，6'-双-O-(3-羟基-2-十四烷基十八烷酰基)-α，α-三卤糖[TD-(B30)]，6，6'-双-O-(2-二十二烷基-3-羟基二十六烷酰基)-α、6，6'-双-O-(2-二十二烷基-3-羟基二十六烷酰)-α，α-三卤糖[TD (BH48)]，6，6'-双-O-(3-十四烷酰氧基-十四烷酰)-α，α-三卤糖[TD (D28)]，6，6'-双脱氧-6，6'-双(霉菌酰氨基)-α，α-三卤糖[TDNM]和 6、合成了 6, 6'-dideoxy-6, 6'-bis (3-hydroxy-2-tetradecyloctadecanoylamino)-α, α-trehalose[TDN（BH32）]，并检测了它们的致死活性和佐剂活性。当小鼠静脉注射剂量为 150 μg 的 9% 水包油型乳剂时，TDM 和 TDNM 具有致死性，但在相同剂量下，其他类似物对小鼠无致死毒性。腹腔注射 TDM 及其合成类似物可增强小鼠腹腔巨噬细胞对肿瘤细胞的细胞溶解活性。TDM 和 TD (BH32) 还能激发 BALB/c 小鼠对仙台病毒感染的非特异性宿主抵抗力。

  DOI：

  10.1248/cpb.33.4544
• 作为产物：
  描述：

  2,3,2',3'-tetra-O-benzyl-α,α-trehalose 在 sodium azide 作用下， 以 甲基叔丁基醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 6,6'-diazido-2,3,2',3'-tetra-O-benzyl-6,6'-dideoxy-α,α-trehalose
  参考文献：
  名称：

  PROCESS FOR THE PRODUCTION OF DATH AND INTERMEDIATES THEREOF

  摘要：

  The present technology is direct to methods of producing 6,6′-diamino-6,6′-deoxy-trehalose (“DATH”) or a salt thereof. The methods include optionally protecting one or more hydroxyl groups of D-trehalose and converting the primary hydroxyl groups of D-trehalose to product DATH or a salt thereof through use of a halogen, azide, and/or protected amine to. The present technology is also direct to intermediate products of the methods.

  公开号：

  US20220389044A1

文献信息

• Lethal and adjuvant activities of cord factor (trehalose-6,6'-dimycolate) and synthetic analogs in mice.
  作者：FUMIO NUMATA、KEIKO NISHIMURA、HIDEHARU ISHIDA、SHIGEKI UKEI、YUKIKO TONE、CHIAKI ISHIHARA、IKUO SAIKI、ISAO SEKIKAWA、ICHIRO AZUMA

  DOI：10.1248/cpb.33.4544

  日期：——

  Mycobacterial glycolipid, trehalose-6, 6'-dimycolate (TDM), and its analogs, 6, 6'-di-O-triacontanoyl-α, α-trehalose [TD (L30)], 6, 6'-bis-O-(2-tetradecylhexadecanoyl)-α, α-trehalose [TD-(B30)], 6, 6'-bis-O-(3-hydroxy-2-tetradecyloctadecanoyl)-α, α-trehalose [TD (BH32)], 6, 6'-bis-O-(2-docosyl-3-hydroxyhexacosanoyl)-α, α-trehalose [TD (BH48)], 6, 6'-bis-O-(3-tetradecanoyloxy-tetradecanoyl)-α, α-trehalose [TD (D28)], 6, 6'-dideoxy-6, 6'-bis (mycoloylamino)-α, α-trehalose [TDNM] and 6, 6'-dideoxy-6, 6'-bis (3-hydroxy-2-tetradecyloctadecanoylamino)-α, α-trehalose [TDN (BH32)], were synthesized, and their lethal and adjuvant activities were examined. TDM and TDNM were lethal when injected intravenously into mice at a dose of 150 μg as 9% oil-in-water emulsion, but the other analogs showed no lethal toxicity to mice at the same dose. The cytolytic activity of mouse peritoneal macrophages against tumor cells was potentiated by intraperitoneal injection of TDM and its synthetic analogs. TDM and TD (BH32) also stimulated nonspecific host resistance against Sendai virus infection in BALB/c mice.

  分枝杆菌糖脂，曲哈洛糖-6，6'-二甲氧基酸酯（TDM）及其类似物，6，6'-二-O-三碳酰基-α，α-曲哈洛糖[TD (L30)]，6，6'-双-O-(2-十四烷基十六烷酰基)-α、6，6'-双-O-(3-羟基-2-十四烷基十八烷酰基)-α，α-三卤糖[TD-(B30)]，6，6'-双-O-(2-二十二烷基-3-羟基二十六烷酰基)-α、6，6'-双-O-(2-二十二烷基-3-羟基二十六烷酰)-α，α-三卤糖[TD (BH48)]，6，6'-双-O-(3-十四烷酰氧基-十四烷酰)-α，α-三卤糖[TD (D28)]，6，6'-双脱氧-6，6'-双(霉菌酰氨基)-α，α-三卤糖[TDNM]和 6、合成了 6, 6'-dideoxy-6, 6'-bis (3-hydroxy-2-tetradecyloctadecanoylamino)-α, α-trehalose[TDN（BH32）]，并检测了它们的致死活性和佐剂活性。当小鼠静脉注射剂量为 150 μg 的 9% 水包油型乳剂时，TDM 和 TDNM 具有致死性，但在相同剂量下，其他类似物对小鼠无致死毒性。腹腔注射 TDM 及其合成类似物可增强小鼠腹腔巨噬细胞对肿瘤细胞的细胞溶解活性。TDM 和 TD (BH32) 还能激发 BALB/c 小鼠对仙台病毒感染的非特异性宿主抵抗力。
• PROCESS FOR THE PRODUCTION OF DATH AND INTERMEDIATES THEREOF
  申请人：Galderma Holding SA

  公开号：US20220389044A1

  公开（公告）日：2022-12-08

  The present technology is direct to methods of producing 6,6′-diamino-6,6′-deoxy-trehalose (“DATH”) or a salt thereof. The methods include optionally protecting one or more hydroxyl groups of D-trehalose and converting the primary hydroxyl groups of D-trehalose to product DATH or a salt thereof through use of a halogen, azide, and/or protected amine to. The present technology is also direct to intermediate products of the methods.
• Convenient Divergent Synthesis of a Library of Trehalosamine Analogues
  作者：Yu Hui、Cheng-Wei Tom Chang

  DOI：10.1021/ol026095m

  日期：2002.6.1

  A library of seven trehalosamine analogues with various natural and non-natural binding motifs was synthesized through an expedient divergent synthetic approach, The final products were prepared in sufficient quantities and purities for different types of assay against various pathogens. Several stereo- and regioselective reactions on the trehalose scaffold were developed for rapid synthesis of all of the designed compounds.