benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside | 66026-11-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
• 英文别名: (4aR,6S,7R,8R,8aS)-7-amino-2,2-dimethyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 66026-11-7
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: MKWVOCKAMGNAAQ-RYPNDVFKSA-N

物化性质

• 沸点：
  462.4±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 sodium hydride 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.5h， 生成 benzyl 3-O-(D-1-carboxyethyl)-2-deoxy-4,6-isopropylidene-2-(tetradecanoylamino)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and immunoadjuvant activities of novel N-acylmuramoyl dipeptides related to the lipid A constituent of the bacterial lipopolysaccharide

  摘要：

  DOI：

  10.1016/s0008-6215(00)85936-4
• 作为产物：
  描述：

  2-benzyloxycarbonylamino-2-deoxy-D-glucose 在 钯 盐酸 、 calcium sulfate 、 氢气 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 0.33h， 生成 benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  脂质A 1-去磷酸衍生物的化学合成

  摘要：

  合成了1-Dephospho大肠杆菌脂质A（），显示与从细菌细胞中分离出的相应衍生物相同。这提供了明确的证据来支持我们最近提出的大肠杆菌脂质A（）的结构。

  DOI：

  10.1016/s0040-4039(00)61962-7

文献信息

• Synthesis and Structure-activity Relationship of<i>N</i>-(Acyl)muramoyl-dipeptides
  作者：Hiroyuki Okumura、Ichiro Azuma

  DOI：10.1080/00021369.1983.10865714

  日期：1983.4

  A variety of N-(acyOmuramoyl-dipeptides were synthesized and their immunoadjuvant activities were examined on the induction of delayed-type hypersensitivity to N-acetyl-l-tyrosine-3- azobenzene-4′-arsonate in guinea pigs. It was found that introduction of acyl groups to the 2-amino group in muramoyl-l-valyl- or -l-seryl-d-isoglutamine reduced the activity with the increasing length of the acyl group, although all N-(acyl)muramoyl-l-alanyl-d-isoglutamines were active as an adjuvant. The results suggest that development of the adjuvant activity of N-(acyl)muramoyl- dipeptides is closely related to both the length of the acyl group and the bulkiness of the peptide moiety.

  多种N-(酰基胞壁酰)二肽被合成，并检测了它们在诱发豚鼠对N-乙酰-L-酪氨酸-3-偶氮苯-4′-砷酸的迟发型超敏反应中的免疫佐剂活性。研究发现，将酰基引入胞壁酰-L-缬氨酰-或-L-丝氨酰-D-异谷氨酰胺的2-氨基组，随着酰基链长的增加，活性降低，尽管所有N-(酰基)胞壁酰-L-丙氨酰-D-异谷氨酰胺都具有佐剂活性。结果表明，N-(酰基)胞壁酰二肽的佐剂活性的开发与酰基链的长度和肽部分的体积密切相关。
• Antigen derivatives and processes for their preparation
  申请人：Ciba-Geigy Corporation

  公开号：US04397844A1

  公开（公告）日：1983-08-09

  The invention relates to novel antigen derivatives comprising an antigen and at least one muramylpeptide covalently bonded thereto, if appropriate via a spacer, to pharmaceutical preparations which contain such compounds and to their use as a vaccine. The novel antigen derivatives produce a pronounced increase in the immuno-response to the antigen, and in particular also a cell-medicated immunity under clinically acceptable conditions of administration.

  这项发明涉及包括抗原和至少一个辅酶肽共价结合在一起的新型抗原衍生物，如适当的话通过间隔物结合，以及包含这种化合物的药物制剂以及它们作为疫苗的用途。这种新型抗原衍生物能够在临床可接受的给药条件下显著增加对抗原的免疫反应，特别是在细胞介导免疫方面。
• Synthesis of 2-deoxy-4-O-phosphono-3-O-tetradecanoyl-2-[(3R- and (3S)-3-tetradecanoyloxytetradecanamido]-d-glucose: a diastereoisomeric pair of 4-O-phosphono-d-glucosamine derivatives (GLA-27) related to bacterial lipid A
  作者：Makoto Kiso、Shinji Tanaka、Masanori Tanahashi、Yushun Fujishima、Yuji Ogawa、Akira Hasegawa

  DOI：10.1016/s0008-6215(00)90390-2

  日期：1986.5

  The diastereoisomeric, 4-O-phosphono-D-glucosamine derivatives named in the title have been synthesized, starting from benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-beta-D-glucopyranoside and (3RS)-3-hydroxytetradecanoic acid.

  由苄基2-氨基-2-脱氧-4,6-O-异亚丙基-β-D-吡喃葡萄糖苷和（3RS）-开始合成了标题中所述的非对映异构体4-O-膦酰基-D-葡萄糖胺衍生物3-羟基十四烷酸。
• Synthesis and biological activity of O-(N-acetyl-β-muramoyl-l-alanyl-d-isoglutamine)-(1→6)-2-acylamino-2-deoxy-d-glucoses
  作者：Akira Hasegawa、Masahiko Ozaki、Yasuhiko Goh、Makoto Kiso、Ichiro Azuma

  DOI：10.1016/s0008-6215(00)81038-1

  日期：——

  -isopropylidene group, gave the corresponding 3- O -benzoyl derivatives ( 4 , 5 , and 7 ). Hydrogenation of benzyl 2-acetamido-4,6-di- O -acetyl-2-deoxy-3- O -[ d -1-(methoxycarbonyl)ethyl]-α- d -glucopyranoside, followed by chlorination, gave a product that was treated with mercuric actate to yield 2-acetamido-1,4,6-tri- O -acetyl-2-deoxy-3- O -[ d -1-(methoxycarbonyl)ethyl]-β- d -glucopyranose ( 11 ). Treatment

  摘要苄基2-乙酰氨基-2-脱氧-4,6-O-异亚丙基-α-d-吡喃葡萄糖苷的苄基化，苄基2-脱氧-2-（dl -3-羟基十四烷酰氨基）-4,6-O-异亚丙基-α -d-吡喃葡萄糖苷和苄基2-脱氧-4,6-O-异亚丙基-2-十八烷酰基氨基-β-d-吡喃葡萄糖苷，随后水解4,6-O-异亚丙基，得到相应的3-O-苯甲酰基衍生物（4，5和7）。苄基2-乙酰氨基-4,6-二-O-乙酰基-2-脱氧-3-O- [d -1-（甲氧羰基）乙基]-α-d-吡喃葡萄糖苷的氢化反应，得到的产物为用乙酸汞处理了2-乙酰氨基-1,4,6-三-O-乙酰基-2-脱氧-3-O- [d -1-（甲氧基羰基）乙基]-β-d-吡喃葡萄糖（11） 。用氯化铁处理11，得到恶唑啉衍生物，其与4、5，和7得到（1→6）-β-连接的二糖衍生物13、15和17。通过4-O-乙酰化作用水解13、15和17衍生化合物中的甲酯基团，得到相应的游
• 6-Deoxyglucosamine-peptide derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04314998A1

  公开（公告）日：1982-02-09

  Novel 6-deoxyglucosamine-peptide derivatives of the formula ##STR1## wherein R is hydrogen or an organic acid residue or alkoxycarbonyl; R.sup.1 is hydrogen or acyl; R.sup.2 is hydrogen or lower alkyl; R.sup.3 and R.sup.4 are each hydrogen or lower alkyl which may be substituted with hydroxyl; R.sup.5 and R.sup.6 are each carboxyl which may be esterified or amidated; R.sup.7 is hydrogen or aralkyl; and (D) and (L) each indicate configurations if their respective carbon atoms are asymmetric or a salt thereof having immunostimulatory activity.

  化合物的名称为6-去氧葡萄糖胺-肽衍生物，其化学式为##STR1## 其中R为氢或有机酸残基或烷氧羰基；R.sup.1为氢或酰基；R.sup.2为氢或低级烷基；R.sup.3和R.sup.4均为氢或低级烷基，可被羟基取代；R.sup.5和R.sup.6均为羧基，可被酯化或酰胺化；R.sup.7为氢或芳基烷基；(D)和(L)表示它们各自的碳原子是不对称的构型，或具有免疫刺激活性的盐。