allyl 2-amino-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside | 138527-55-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-amino-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
• 英文别名: allyl 2-amino2-deoxy-4,6-O-isopropylidenbe-α-D-glucopyranoside；allyl 2-amino-4,6-O-isopropylidene-α-D-glucopyranoside；Allyl 2-deoxy-2-amino-4,6-O-isopropylidene-α-D-glucopyranoside；(4aR,6S,7R,8R,8aS)-7-amino-2,2-dimethyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 138527-55-6
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: VNXUKMIDIOWLTI-ILAIQSSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 2-amino-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 allyl 2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-4,6-O-isopropylidene-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 2-Deoxy-2-((2S,3R)-(2-fluoro-3-hydroxytetradecanoly)amino)-3-O-((3R)-3-tetradecanoyloxytetradecanoyl)-D-glucopyranose 4-(Dihydrogen Phosphate) and 2-Deoxy-2-((2R,3S)-(2-fluoro-3-hydroxytetradecanoyl)amino)-3-O-((3R)-3-tetradecanoyloxytetradecanoyl)-D-glucopyranose 4-(Dihydrogen Phosphate).

  摘要：

  合成了2-脱氧-2-[(2S, 3R)-(2-氟-3-羟基十四酸酰基)氨基]-3-O-[(3R)-3-十四酸酰氧基十四酸酰基]-D-葡萄糖吡喃糖4-(二氢磷酸盐)和2-脱氧-2-[(2R, 3S)-(2-氟-3-羟基十四酸酰基)氨基]-3-O-[(3R)-3-十四酸酰氧基十四酸酰基]-D-葡萄糖吡喃糖4-(二氢磷酸盐)。在巨噬细胞的前列腺素D2释放测试中，(2S, 3R)-化合物(9a)的活性略高于GLA-60，而(2R, 3S)-化合物(9b)几乎没有活性。

  DOI：

  10.1248/cpb.40.333
• 作为产物：
  描述：

  allyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 在 barium dihydroxide 作用下， 以 水 为溶剂， 反应 120.0h， 以83%的产率得到allyl 2-amino-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  球形红球菌IFO 15564对N-乙酰基-D-氨基葡萄糖衍生物的降解：底物特异性及其在烯丙基α-N-乙酰基-D-氨基葡萄糖苷合成中的应用。

  摘要：

  研究了以Rhodococcus rhodochrous IFO 15564代谢N-乙酰基-D-葡萄糖胺（GlcNAc）衍生物的代谢的底物特异性，IFO 15564具有N-乙酰基-D-葡萄糖胺脱乙酰基酶作为关键步骤酶。该微生物降解了具有修饰的N-酰基的多种底物。该菌株的代谢活性降低到在GlcNAc的1,3,4,6-位置被取代的底物低，建议GlcNAc本身通过开链醛形式代谢。基于这些结果，通过用Jack豆β-N-乙酰基-D-氨基葡萄糖苷酶选择性水解β-端基异构体，开发了从α，β-异头物混合物中分离烯丙基α-N-乙酰基-D-氨基葡萄糖的简化程序。然后用这种微生物降解反应混合物中所得的N-乙酰基-D-葡糖胺。

  DOI：

  10.1271/bbb.62.1581

文献信息

• Syntheses of 1-O-carboxyalkyl GLA-60 analogues
  作者：Masao Shiozaki、Noriko Deguchi、Wallace M. Macindoe、Masami Arai、Hideki Miyazaki、Takashi Mochizuki、Tohru Tatsuta、Junko Ogawa、Hiroaki Maeda、Shin-ichi Kurakata

  DOI：10.1016/0008-6215(95)00402-5

  日期：1996.3

  As part of our ongoing study to survey potent LPS antagonists, the following six compounds were synthesized in an efficient manner: 3-carboxypropyl and carboxymethyl 2-deoxy-2-(2,2-difluorotetradecanamido)-4-O-phosphono-3-O-[(R)-3- (tetradecanoyloxy)tetradecanoyl]-alpha- and beta-D-glucopyranosides (11 and 23; 32 and 36), as well as the non-fluorinated equivalents, carboxymethyl 2-deoxy-4-O-phosph

  作为我们正在进行的调查有效LPS拮抗剂的研究的一部分，以有效的方式合成了以下六种化合物：3-羧丙基和羧甲基2-脱氧-2-（2,2-二氟四癸酰胺基）-4-O-膦酰基-3- O-[（R）-3-（十四烷氧基）十四烷酰基]-α-和β-D-吡喃葡萄糖苷（11和23; 32和36），以及未氟化的等同物羧甲基2-脱氧-4-O -膦酰基-2-十四烷酰胺基-3-O-[（R）-3-（十四烷酰氧基）-十四烷酰基]-α-D-吡喃葡萄糖苷（44）和羧甲基2-脱氧-2-[（R）-3-（ （羟基）十四烷酰胺基] -4-O-膦酰基-3-O-[（R）-3-（十四烷酰氧基）十四烷酰基]-α-D-吡喃葡萄糖苷（48）。在这些化合物中，就LPS-拮抗活性而言，最显着的是32种。
• Lipid A analogs having immunoactivating and anti-tumor activity
  申请人：Sankyo Company, Limited

  公开号：US05792840A1

  公开（公告）日：1998-08-11

  Compounds of formula (I): ##STR1## in which: R.sup.1 is hydroxy, protected hydroxy, fluorine, or --OP(O)(OH).sub.2 ; R.sup.2 and R.sup.3 are independently optionally substituted C.sub.6 -C.sub.20 aliphatic acyl; R.sup.4 is hydroxy, protected hydroxy, or --OP(O)(OH).sub.2, where at least one of R.sup.1 and R.sup.4 is --OP(O)(OH).sub.2 ; and R.sup.5 is hydroxy, protected hydroxy, or fluorine; provided that, except where at least one of R.sup.1 and R.sup.5 is fluorine, then at least one of R.sup.2 and R.sup.3 is a substituted C.sub.6 -C.sub.20 aliphatic acyl having (i) at least one halogen substituent and (ii) at least one substituent selected from the group consisting of halogen, hydroxy and C.sub.6 -C.sub.20 aliphatic acyloxy or at least one of R.sup.2 and R.sup.3 is a substituted C.sub.6 -C.sub.20 aliphatic acyl which is substituted by at least one halogen-substituted C.sub.6 -C.sub.20 aliphatic carboxylic acyloxy; have Lipid A-like activity and may be used for the treatment, prophylaxis, diagnosis and support of an animal suffering a disease or disorder arising from a deficiency in the immune system or from a tumor. They may be prepared by phosphorylation of corresponding compounds lacking a phosphoryl group.

  式（I）的化合物：其中：R.sup.1是羟基，保护羟基，氟或--OP（O）（OH）.sub.2；R.sup.2和R.sup.3分别是可选取代的C.sub.6-C.sub.20脂肪族酰基；R.sup.4是羟基，保护羟基，或--OP（O）（OH）.sub.2，其中至少有一个R.sup.1和R.sup.4是--OP（O）（OH）.sub.2；R.sup.5是羟基，保护羟基，或氟；但是，除非R.sup.1和R.sup.5中至少有一个是氟，否则R.sup.2和R.sup.3中至少有一个是具有（i）至少一个卤素取代基和（ii）至少一个取代基的取代C.sub.6-C.sub.20脂肪族酰基，所述取代基选自卤素、羟基和C.sub.6-C.sub.20脂肪族酰氧基，或R.sup.2和R.sup.3中至少有一个是经取代的C.sub.6-C.sub.20脂肪族酰基，该取代基由至少一个卤素取代的C.sub.6-C.sub.20脂肪族羧酰氧基取代；具有类似脂多糖A的活性，可用于治疗、预防、诊断和支持患有免疫系统缺陷或肿瘤引起的疾病或紊乱的动物。它们可以通过对缺乏磷酰基的对应化合物进行磷酸化来制备。
• Lipid A analogues having immunoactivating and anti-tumour activity
  申请人：Sankyo Company Limited

  公开号：EP0437016A2

  公开（公告）日：1991-07-17

  Compounds of formula (I): [in which: R1 is hydroxy, protected hydroxy, fluorine, or -OP(0)(OH)2; R2 and R3 are independently optionally substituted C6 - C20 aliphatic acyl; R4 is hydroxy, protected hydroxy, or -OP(O)(OH)2, where at least one of R1 and R4 is -OP(O)(OH)2; and R5 is hydroxy, protected hydroxy, or fluorine; provided that, except where at least one of R1 and R5 is fluorine, then at least one of R2 and R3 is a substituted C6 - C20 aliphatic acyl having (i) at least one halogen substituent and (ii) at least one of halogen, hydroxy and C6 - C20 aliphatic acyloxy or at least one of R2 and R3 is a substituted C6 - C20 aliphatic acyl which is substituted by at least one halogen-substituted C6 - C20 aliphatic carboxylic acyloxy]; have Lipid A-like activity and may be used for the treatment, prophylaxis, diagnosis and support of an animal suffering a disease or disorder arising from a deficiency in the immune system or from a tumor. They may be prepared by phosphorylation of corresponding compounds lacking a phosphoryl group.

  式(I)化合物： 其中R1 是羟基、受保护的羟基、氟或-OP(0)(OH)2；R2 和 R3 独立地是任选取代的 C6 - C20 脂肪族酰基；R4 是羟基、受保护的羟基或-OP(O)(OH)2，其中 R1 和 R4 中至少有一个是-OP(O)(OH)2；R5 是羟基、受保护的羟基或氟；条件是，除非 R1 和 R5 中至少有一个是氟，否则 R2 和 R3 中至少有一个是被取代的 C6 - C20 脂肪族酰基，该酰基具有 (i) 至少一个卤素取代基和 (ii) 卤素、羟基和 C6 - C20 脂肪族酰氧基中的至少一个，或者 R2 和 R3 中至少有一个是被至少一个卤素取代的 C6 - C20 脂肪族羧基酰氧基取代的 C6 - C20 脂肪族酰基]；具有类似脂质 A 的活性，可用于治疗、预防、诊断和支持因免疫系统缺陷或肿瘤引起的疾病或紊乱的动物。它们可以通过对缺乏磷酸基团的相应化合物进行磷酸化来制备。
• Syntheses of 2,6-dideoxy-6-fluoro-2-[(3R and 3S)-3- hydroxytetradecanamido]-3-O-[(3R)-3-(tetradecanoyloxy)- tetradecanoyl]-d-glucopyranose 4-(dihydrogen phosphate) and 2-deoxy-2-[(3R and 3S)-3-hydroxytetradecanamido]- 3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-α-d-glucopyranosyl fluoride 4-(dihydrogen phosphate): fluorosugar analogues of GLA-60
  作者：Yoshiyuki Kobayashi、Nobory Ishida、Masami Arai、Masao Shiozaki、Tetsuo Hiraoka、Masahiro Nishijima、Sayuri Kuge、Toshiaki Otsuka、Yuzuru Akamatsu

  DOI：10.1016/0008-6215(91)89008-4

  日期：1991.12

  Both 2,6-dideoxy-6-fluoro-2-[(3R)- and (3S)-3-hydroxytetradecanamido]-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glucopyranose 4-phosphate, 11 and 11' (6-fluoro GLA-60 and its 3'-epimer), and 2-deoxy-2[(3R)- and (3S)-(3-hydroxytetradecanamido]-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-alpha-D-glucopyranosyl fluoride 4-(dihydrogen phosphate), 18 and 18' (1-fluoro GLA-60 and its 3'-epimer), were synthesized from ally 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-alpha-D-glucopyranoside.
• Synthesis of linked carbohydrates and evaluation of Their binding for 16S RNA by mass spectrometry
  作者：Baogen Wu、Jun Yang、Dale Robinson、Steve Hofstadler、Rich Griffey、Eric E. Swayze、Yun He

  DOI：10.1016/j.bmcl.2003.09.005

  日期：2003.11

  A library of linked molecules were synthesized from the common sugar moieties existing in the natural amino glycosides. These linked molecules were screened against bacterial 16S RNA for their binding affinity using a mass spectrometry-based technology. Some of these compounds exhibited low micromolar affinity and could serve as leads for further development as antibacterial agents. (C) 2003 Published by Elsevier Ltd.