benzyl 2-acetamido-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside | 58886-33-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-acetamido-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside
• 英文别名: benzyl 2-acetamido-2-deoxy-5,6-isopropylidene-β-D-glucofuranoside；benzyl 2-acetamido-2 deoxy-5,6-0 isopropylidene-β-D-glucofuranoside；N-[(2R,3R,4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxy-2-phenylmethoxyoxolan-3-yl]acetamide
• CAS: 58886-33-2
• 化学式: C₁₈H₂₅NO₆
• 分子量: 351.4
• InChiKey: KRHGWOAKYIWWDG-WRQOLXDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 8.0h， 生成 2-acetamido-2-deoxy-5,6-O-isopropylidene-3-O-(tetrahydropyran-2-yl)-D-glucofuranose
  参考文献：
  名称：

  Okumura, Hiroyuki; Kiso, Makoto; Hasegawa, Akira, Agricultural and Biological Chemistry, 1983, vol. 47, # 4, p. 839 - 846

  摘要：

  DOI：

文献信息

• Synthesis of carbohydrate analogs (positional, configurational, and optical) of N-acetylmuramoyl-l-alanyl-d-isoglutamine, and their immunoadjuvant activities
  作者：Akira Hasegawa、Yoshimi Kaneda、Yasuhiko Goh、Kaoru Nishibori、Makoto Kiso、Ichiro Azuma

  DOI：10.1016/s0008-6215(00)80713-2

  日期：1981.8

  3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D- and -L-glucopyranose were synthesized, in order to clarify the structural requirements for the immunoadjuvant activity of the carbohydrate moiety in N-acetylmuramoyl-L-alanyl-D-isoglutamine. Immunoadjuvant activity of the N-acetylmuramoyl-dipeptide analogs was examined in guinea-pigs.

  2-乙酰氨基-2-脱氧-4-和-6-O-（D-2-丙酰基-L-丙氨酰基-D-异谷氨酰胺）-D-吡喃葡萄糖，2-乙酰氨基-2-脱氧-3-O-（D -2-丙酰基-L-丙氨酰基-D-异谷氨酰胺）-D-戊吡喃糖，-D-戊吡喃糖，-D-吡喃半乳糖，-D-甘露吡喃糖和-L-吡喃吡喃糖和3-O-（D-2-丙酰基合成-L-丙氨酰基-D-异谷氨酰胺-D-和-L-吡喃葡萄糖，以阐明N-乙酰基村酰基-L-丙氨酰基-D-异谷氨酰胺中碳水化合物部分的免疫佐剂活性的结构要求。在豚鼠中检查了N-乙酰基村酰基-二肽类似物的免疫佐剂活性。
• Immunologically active dipeptidyl
  申请人：Merck & Co., Inc.

  公开号：US04310514A1

  公开（公告）日：1982-01-12

  Immunologically active compounds of the formula: ##STR1## wherein R.sub.1 is C.sub.1-7 alkyl, substituted C.sub.1-7 alkyl; phenyl; or substituted phenyl; R.sub.2 is hydrogen; or C.sub.1-10 alkyl; R.sub.3 and R.sub.4 may be the same or different and are each independently acyl of the formula: ##STR2## where X is --O--, --S--, or ##STR3## R.sub.9, R.sub.10 and R.sub.12 may be the same or different and are each independently hydrogen; C.sub.1-20 alkyl; C.sub.1-20 alkylcarbonyloxy; amino; benzyl; C.sub.1-20 alkoxymethyl; or C.sub.1-20 alkylamido; r is 0 or 1; s is 0 or 1; and t is 0-20, provided that s may only be 0 when r and t are greater than 0, or when r is 0 and R.sub.11 is amino, phenyl, substituted phenyl, 1-adamantyl, or heterocycle selected from the group consisting of 2- or 3-furyl, 2- or 3-thienyl, 2- or 3-pyrrolidinyl, 2-, 3-, or 4-pyridyl, and 1-tetrazolyl, said hetero-cycle optionally substituted with C.sub.1-20 alkylcarbonyl; and R.sub.11 is hydrogen; C.sub.1-30 alkyl; C.sub.2-30 alkenyl; C.sub.1-30 alkoxy; phenyl; C.sub.1-20 alkylsulfonyl; or cholesteryl; and R.sub.4 may additionally be hydrogen; R.sub.5 is hydrogen; or R.sub.5 -R.sub.6 together is --CH.sub.2 --CH.sub.2 --CH.sub.2 ; R.sub.6 is hydrogen; C.sub.1-7 alkyl; hydroxymethyl; mercapto-methyl; benzyl; or substituted benzyl; R.sub.7 and R.sub.8 may be the same or different and are each independently COOR or CONR'R", where R is hydrogen or C.sub.1-7 alkyl, and R' and R" are each independently hydrogen or C.sub.1-3 alkyl; when R.sub.2 is C.sub.1-10 alkyl, the stereochemistry at asymmetric center I can be either D or L; when R.sub.6 is not hydrogen, the stereochemistry at asymmetric center Ii is L; the stereochemistry at asymmetric center III is D.

  公式为：##STR1##其中R.sub.1为C.sub.1-7烷基，取代C.sub.1-7烷基;苯基;或取代苯基;R.sub.2为氢;或C.sub.1-10烷基;R.sub.3和R.sub.4可以相同也可以不同，分别独立地为配基的酰基公式：##STR2##其中X为--O--，--S--或##STR3##R.sub.9、R.sub.10和R.sub.12可以相同也可以不同，分别独立地为氢; C.sub.1-20烷基; C.sub.1-20烷基羧酸酯; 氨基; 苄基; C.sub.1-20烷氧甲基; 或C.sub.1-20烷基酰胺; r为0或1; s为0或1; t为0-20，但当r和t大于0，或当r为0且R.sub.11为氨基，苯基，取代苯基，1-金刚烷基或从2-或3-呋喃基，2-或3-噻吩基，2-或3-吡咯烷基，2-，3-或4-吡啶基和1-四唑基选择的杂环组成的群，所述杂环可选地取代C.sub.1-20烷基羧酸; R.sub.11为氢; C.sub.1-30烷基; C.sub.2-30烯基; C.sub.1-30烷氧基; 苯基; C.sub.1-20烷基磺酰基; 或胆固醇基; R.sub.4还可以是氢; R.sub.5为氢; 或R.sub.5-R.sub.6一起为--CH.sub.2--CH.sub.2--CH.sub.2; R.sub.6为氢; C.sub.1-7烷基; 羟甲基; 巯基甲基; 苄基; 或取代苯基; R.sub.7和R.sub.8可以相同也可以不同，分别独立地为COOR或CONR'R"，其中R为氢或C.sub.1-7烷基，而R'和R"各自独立地为氢或C.sub.1-3烷基; 当R.sub.2为C.sub.1-10烷基时，不对称中心I的立体化学可以为D或L; 当R.sub.6不为氢时，不对称中心Ii的立体化学为L; 不对称中心III的立体化学为D。
• Synthesis and immunoadjuvant activities of 2-acetamido-5-O-acetyl-6-O-acyl-2-deoxy-3-O-[(R)-2-propionyl-L-alanyl-D-isoglutamine]-D-glucofuranoses as potential prodrug forms of 6-O-acyl derivatives of N-acetylmuramyl dipeptide
  作者：Philippe L. Durette、Conrad P. Dorn、Arthur Friedman、Abner Schlabach

  DOI：10.1021/jm00351a005

  日期：1982.9

  micrograms; moreover, its potent adjuvant activity was not diminished at the lower dose. The three 5-O-acetylated 6-O-acylated dipeptidyl furanose derivatives also significantly stimulated production of circulating antibodies against hepatitis B vaccine in mice; titers were comparable to those observed with the alum-adsorbed vaccine. The range of immunoadjuvant activities obtained with 8-10 and control compounds

  设计成前药形式的2-乙酰氨基-5-O-乙酰基-6-O-酰基-2-脱氧-3-O-[（R）-2-丙酰基-L-丙氨酰基-D-异谷氨酰胺] -D-葡糖呋喃糖酶由苄基2-乙酰氨基-2-脱氧-5、6-O-异亚丙基-β-D-葡萄糖呋喃糖苷合成了N-乙酰基村mura基二肽（MDP）相应的具有免疫佐剂活性的6-O-酰基衍生物在水性介质中对小鼠给药，以提高针对牛血清白蛋白的抗体产生。5，6-二-O-乙酰基衍生物8在50微克/剂量下表现出类似于MDP的活性。对5-O-乙酰基-6-O-硬脂酰化合物9测得的抗体滴度与使用6-O-硬脂酰-MDP在50微克下测得的抗体效价相当，并且两种化合物在5微克下均比MDP更具活性。亲脂性更强的5-O-乙酰基-6-O- [2-（山hen酰氧基）异丁酰基]化合物10在50和5微克下的活性都比MDP高得多；此外，在较低剂量下其有效的佐剂活性并未降低。三种5-O-乙酰化的6-O-酰化二肽
• Immunologically active dipeptidyl 5-0,6-0-acyl-2-amino-2-deoxy-D-glucofuranose derivatives and methods of preparation
  申请人：Merck & Co., Inc.

  公开号：EP0039637A1

  公开（公告）日：1981-11-11

  Immunologically active compounds of the formula: wherein R1 is CI-7 alkyl, substituted C1-7 alkyl; phenyl; or substituted phenyl; R2 is hydrogen; or C1-10 alkyl; R3 and R4 may be the same or different and are each independently acyl of the formula: where X is -O-, -S-, or R9, R10 and R12 may be the same or different and are each independently hydrogen; C1-20 alkyl; C1-20 alkylcarbonyloxy; amino; benzyl; C1-20 alkoxymethyl; or C1-20 alkylamido; r is 0 or 1; s is 0 or 1; and t is 0-20, provided that s may only be 0 when r and t are greater than 0, or when r is 0 and R11 is amino, phenyl, substituted phenyl, 1-adamantyl, or heterocycle selected from the group consisting of 2- or 3-furyl, 2- or 3-thienyl, 2- or 3-pyrrolidinyl, 2-, 3-, or 4-pyridyl, and 1-tetrazolyl, said heterocycle optionally substituted with C1-20 alkylcarbonyl; and R11 is hydrogen; C1-30 alkyl; C2-30 alkenyl; C1-30 alk- oyx; phenyl; C1-20 alkylsulfonyl; or cholesteryl; and R4 may additionally be hydrogen; Rs is hydrogen; or R5-R6 together is -CH2-CH2-CH2; R6 is hydrogen; CI-7 alkyl; hydroxymethyl; mercaptomethyl; benzyl; or substituted benzyl; R7 and R8 may be the same or different and are each independently COOR or CONR'R", where R is hydrogen or C1-7 alkyl, and R' and R" are each independently hydrogen or C1-3 alkyl; when R2 is C1-10 alkyl, the stereochemistry at asymmetric center I can be either D or L; when R6 is not hydrogen, the stereochemistry at asymmetric center II is L; the stereochemistry at asymmetric center III is D.

  式中的免疫活性化合物： 式中 R1 是 CI-7 烷基、取代的 C1-7 烷基；苯基；或取代的苯基； R2 是氢；或 C1-10 烷基； R3 和 R4 可以相同或不同，各自独立为式中的酰基： 其中 X 是 -O-、-S- 或 R9、R10 和 R12 可以相同或不同，各自独立地为氢；C1-20 烷基；C1-20 烷基羰氧基；氨基；苄基；C1-20 烷氧基甲基；或 C1-20 烷基氨基； r 为 0 或 1；s 为 0 或 1；t 为 0-20，但只有当 r 和 t 大于 0 时，或当 r 为 0 且 R11 为氨基、苯基、取代苯基、1-金刚烷基或选自 2-或 3-呋喃基、2-或 3-噻吩基、2-或 3-吡咯烷基、2-、3-或 4-吡啶基和 1-四唑基组成的杂环时，s 才可能为 0，所述杂环可选择被 C1-20 烷基羰基取代；以及 R11 是氢；C1-30 烷基；C2-30 烯基；C1-30 炔基；苯基；C1-20 烷基磺酰基；或胆固醇基；以及 R4 还可以是氢； Rs 是氢；或 R5-R6 合在一起是-CH2- - ； R6 是氢；CI-7 烷基；羟甲基；巯甲基；苄基；或取代的苄基； R7和R8可以相同或不同，且各自独立地为COOR或CONR'R"，其中R为氢或C1-7烷基，R'和R "各自独立地为氢或C1-3烷基；当R2为C1-10烷基时，不对称中心I的立体化学结构可以为D或L；当R6不是氢时，不对称中心II的立体化学结构为L；不对称中心III的立体化学结构为D。
• DURETTE, PHILIPPE L.
  作者：DURETTE, PHILIPPE L.

  DOI：——

  日期：——