2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-mannopyranose | 42890-10-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-mannopyranose
• 英文别名: benzyl N-[(2S,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]carbamate
• CAS: 42890-10-8
• 化学式: C₁₄H₁₉NO₇
• 分子量: 313.307
• InChiKey: FRTOTMQAWIIMKK-MLGHIDQZSA-N

物化性质

• 沸点：
  606.0±55.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  D-mannosamine hydrochloride 、 氯甲酸苄酯 在 sodium acetate 作用下， 以 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 48.0h， 生成 2-<(benzyloxycarbonyl)amino>-2-deoxy-β-D-mannopyranose 、 2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-mannopyranose
  参考文献：
  名称：

  Versatile intermediates in the selective modification of the amino function of 2-amino-2-deoxy-d-mannopyranose and the 3-position of 2-acetamido-2-deoxy-d-mannose: Potential membrane modifiers in neoplastic control

  摘要：

  A general method has been developed to selectively modify the amino group of 2-amino-2-deoxy-D-mannopyranose (D-mannosamine), a precursor of the terminal membrane sugar, sialic acid. 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-alpha-D-mannopyranose oxalate was prepared via two routes that allowed introduction of various acyl groups onto the amino function. These compounds were evaluated for their antineoplastic properties. The most significant preclinical therapeutic finding was the antileukemic activity found in mice for tetra-O-acetyl-2-epi-streptozotocin (the acetylated alpha-mannosamine epimer of streptozotocin). Administration of 50 mg/kg/day X 5 to leukemia L1210-bearing DBA/2Ha mice resulted in 5/5 35-day survivors. Neutralization of 1,3,3,6-tetra-O-acetyl-2-amino-2-deoxy-alpha-D-mannopyranose oxalate under aqueous conditions led to 2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-alpha-D-mannopyranose, the oxidation of which gave 2-acetamido-4,6-di-O-acetyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose. This agent demonstrated an IC50 of 25 mu M with a murine L1210 cell culture. Administration of 100 mg/kg/day X 5 resulted in 42% ILS in DBA/2 mice with ip L1210 leukemia. Several other nonacetylated derivatives were also prepared by direct N-acylation, producing, for example, fluorescently tagged N-dansylmannosamine.

  DOI：

  10.1016/0008-6215(95)00154-l

文献信息

• [EN] A METHOD FOR OBTAINING CRYSTALLINE LACTO-N-TETRAOSE AND LACTO-N-NEOTETRAOSE PRECURSORS AND MIXTURES THEREOF<br/>[FR] PROCÉDÉ POUR OBTENIR DES PRÉCURSEURS DE LACTO-N-TÉTRAOSE ET DE LACTO-N-NEOTÉTRAOSE CRISTALLIN ET DES MÉLANGES DE CEUX-CI
  申请人：GLYCOM AS

  公开号：WO2013091660A1

  公开（公告）日：2013-06-27

  A mixture of, preferably a mixture consisting essentially of, an lacto-N-tetraose (LNT) precursor (1) and an lacto-N-neotetraose (LNnT) precursor (2), (formula 1, 2), where R is a group removable by hydrogenolysis and R3 is either a group removable by hydrogenolysis or H, a method of crystallizing 1 and/or 2 from said mixture, and the use of said mixture for making a mixture consisting essentially of LNnT and LNT for use as a pharmaceutically or nutritionally active ingredient. The precursors can be made by reacting an acceptor of formula 5, (formula 5), wherein R is a group removable by hydrogenolysis, R1 is acyl, Ri is acyl or H, R3 is selected from a group removable by hydrogenolysis, acyl, silyl and an acetal type group and Y is selected from alkanoylamido, haloalkanoylamido, -NAc2, benzamido, alkoxycarbonylamino, haloalkoxycarbonylamino, benzyloxycarbonylamino, azido, phthalimido, tetrachlorophthalimido, 2,3- diphenylmaleimido and 2,3-dimethylmaleimido, with a donor of formula 6, (formula 6), wherein R4 is acyl and Xi is selected from halogen, -OC(=NH)CCl3, -OAc, -OBz or -SR5, wherein R5 is selected from alkyl, substituted phenyl and unsubstituted phenyl, followed by one or more deprotection steps.

  一种混合物，优选基本上由乳糖-N-四糖（LNT）前体（1）和乳糖-N-新四糖（LNnT）前体（2）（式1，2）组成，其中R是通过氢解可移除的基团，R3是可通过氢解移除的基团或H，从该混合物中结晶1和/或2的方法，以及该混合物用于制备基本上由LNnT和LNT组成的混合物，作为药用或营养活性成分的用途。这些前体可以通过反应一个受体式5（式5），其中R是通过氢解可移除的基团，R1是酰基，Ri是酰基或H，R3是从可通过氢解移除的基团、酰基、硅基和缩醛型基团中选择的，Y是从烷酰胺基、卤代烷酰胺基、-NAc2、苯甲酰胺基、烷氧羰基氨基、卤代烷氧羰基氨基、苄氧羰基氨基、叠氮基、邻苯二甲酰亚胺基、四氯邻苯二甲酰亚胺基、2,3-二苯基马来酰亚胺基和2,3-二甲基马来酰亚胺基中选择的，与一个供体式6（式6）反应，其中R4是酰基，Xi是从卤素、-OC(=NH)CCl3、-OAc、-OBz或-SR5中选择的，其中R5是从烷基、取代的苯基和未取代的苯基中选择的，随后进行一个或多个脱保护步骤来制备。
• METHOD FOR DETECTING CANCER CELL USING FLUORESCENTLY LABELED L-GLUCOSE DERIVATIVE, AND CANCER CELL-IMAGING AGENT COMPRISING FLUORESCENTLY LABELED L-GLUCOSE DERIVATIVE
  申请人：Yamada Katsuya

  公开号：US20140154717A1

  公开（公告）日：2014-06-05

  The purpose of the present invention is to provide a method for highly accurately detecting a cancer cell. The method of the present invention is characterized by comprising imaging with the use of a fluorescently labeled L-glucose derivative. By using the method and imaging agent according to the present invention, a high contrast between a cancer cell and a normal cell can be obtained compared with the case that imaging is conducted with the use of a fluorescently labeled D-glucose derivative. According to this method, moreover, no fasting is needed for the determination. Thus, the imaging can be quickly carried out without imposing a burden on a patient.

  本发明的目的是提供一种高精度检测癌细胞的方法。本发明的方法的特点在于使用荧光标记的L-葡萄糖衍生物进行成像。通过使用本发明的方法和成像剂，与使用荧光标记的D-葡萄糖衍生物进行成像相比，可以获得癌细胞和正常细胞之间的高对比度。此外，根据本方法，不需要进行禁食以进行确定，因此可以在不对患者造成负担的情况下快速进行成像。
• US4855283A
  申请人：——

  公开号：US4855283A

  公开（公告）日：1989-08-08
• [EN] METHOD FOR DETECTING CANCER CELL USING FLUORESCENTLY LABELED L-GLUCOSE DERIVATIVE, AND CANCER CELL-IMAGING AGENT COMPRISING FLUORESCENTLY LABELED L-GLUCOSE DERIVATIVE<br/>[FR] PROCÉDÉ POUR DÉTECTER UNE CELLULE CANCÉREUSE EN UTILISANT UN DÉRIVÉ DE L-GLUCOSE MARQUÉ PAR FLUORESCENCE, ET AGENT D'IMAGERIE DE CELLULES CANCÉREUSES COMPRENANT UN DÉRIVÉ DE L-GLUCOSE MARQUÉ PAR FLUORESCENCE
  申请人：UNIV HIROSAKI

  公开号：WO2012133688A1

  公开（公告）日：2012-10-04

  　本発明の目的はがん細胞を精度よく検出するための方法を提供することである。本発明は、蛍光標識されたＬ－グルコース誘導体を用いてイメージングを行うことを特徴とする。本発明の方法及びイメージング剤を用いることにより、蛍光標識されたＤ－グルコース誘導体を用いてイメージングを行う場合に比較して、がん細胞と正常細胞との間で高いコントラストを得ることができる。また、判定に際して絶食を行う必要がないので、患者に負担を強いることなく、迅速に実施することができる。
• Versatile intermediates in the selective modification of the amino function of 2-amino-2-deoxy-d-mannopyranose and the 3-position of 2-acetamido-2-deoxy-d-mannose: Potential membrane modifiers in neoplastic control
  作者：Norman J. Angelino、Ralph J. Bernacki、Moheswar Sharma、Onda Dodson-Simmons、Walter Korytnyk

  DOI：10.1016/0008-6215(95)00154-l

  日期：1995.10

  A general method has been developed to selectively modify the amino group of 2-amino-2-deoxy-D-mannopyranose (D-mannosamine), a precursor of the terminal membrane sugar, sialic acid. 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-alpha-D-mannopyranose oxalate was prepared via two routes that allowed introduction of various acyl groups onto the amino function. These compounds were evaluated for their antineoplastic properties. The most significant preclinical therapeutic finding was the antileukemic activity found in mice for tetra-O-acetyl-2-epi-streptozotocin (the acetylated alpha-mannosamine epimer of streptozotocin). Administration of 50 mg/kg/day X 5 to leukemia L1210-bearing DBA/2Ha mice resulted in 5/5 35-day survivors. Neutralization of 1,3,3,6-tetra-O-acetyl-2-amino-2-deoxy-alpha-D-mannopyranose oxalate under aqueous conditions led to 2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-alpha-D-mannopyranose, the oxidation of which gave 2-acetamido-4,6-di-O-acetyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose. This agent demonstrated an IC50 of 25 mu M with a murine L1210 cell culture. Administration of 100 mg/kg/day X 5 resulted in 42% ILS in DBA/2 mice with ip L1210 leukemia. Several other nonacetylated derivatives were also prepared by direct N-acylation, producing, for example, fluorescently tagged N-dansylmannosamine.