(2R,3R,4R,5R,6R)-6-(hydroxymethyl)-3-[(4-methoxyphenyl)methylideneamino]oxane-2,4,5-triol | 233595-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3R,4R,5R,6R)-6-(hydroxymethyl)-3-[(4-methoxyphenyl)methylideneamino]oxane-2,4,5-triol
• CAS: 233595-32-9
• 化学式: C₁₄H₁₉NO₆
• 分子量: 297.308
• InChiKey: NMMULIPYJSFGRK-RKQHYHRCSA-N

物化性质

• 沸点：
  558.1±50.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R,6R)-6-(hydroxymethyl)-3-[(4-methoxyphenyl)methylideneamino]oxane-2,4,5-triol 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 26.25h， 生成 1,3,4,6-tetra-O-acetyl-2-(3-acetylthio)propanamido-2-deoxy-β-D-galactopyranose
  参考文献：
  名称：

  Inhibition of Mucin-Type O-Glycosylation through Metabolic Processing and Incorporation of N-Thioglycolyl-d-galactosamine Peracetate (Ac₅GalNTGc)

  摘要：

  Mucin-type O-glycans form one of the most abundant and complex post-translational modifications (PTM) on cell surface proteins that govern adhesion, migration, and trafficking of hematopoietic cells. Development of targeted approaches to probe functions of O-glycans is at an early stage. Among several approaches, small molecules with unique chemical functional groups that could modulate glycan biosynthesis form a critical tool. Herein, we show that metabolism of peracetyl N-acyl-D-galactosamine derivatives carrying an N-thioglycolyl (Ac(5)GalNTGc, 1) moiety but not N-glycolyl (Ac(5)GalNGc, 2) and N-acetyl (Ac(4)GalNAc, 3) through the N-acetyl-D-galactosamine (GalNAc) salvage pathway induced abrogation of MAL-II and PNA epitopes in Jurkat cells. Mass spectrometry of permethylated O-glycans from Jurkat cells confirmed the presence of significant amounts of elaborated O-glycans (sialyl-T and disialyl-T) which were inhibited upon treatment with 1. O-Glycosylation of CD43, a cell surface antigen rich in O-glycans, was drastically reduced by 1 in a thiol-dependent manner. By contrast, only mild effects were observed for CD45 glycoforms. Direct metabolic incorporation of 1 was confirmed by thiol-selective Michael addition reaction of immunoprecipitated CD43-myc/FLAG. Mechanistically, CD43 glycoforms were unperturbed by peracetylated N-(3-acetylthiopropanoyl) (4), N-(4-acetylthiobutanoyl) (5), and N-methylthioacetyl (6) galactosamine derivatives, N-thioglycolyl-o-glucosarnine (7, C-4 epimer of 1), and alpha-O-benzyl 2-acetamido-2-deoxy-o-galactopyranoside (8), confirming the critical requirement of both free sulthydryl and galactosamine moieties for inhibition of mucin-type O-glycans. Similar, yet differential, effects of 1 were observed for CD43 glycoforms in multiple hematopoietic cells. Development of small molecules that could alter glycan patterns in an antigen-selective and cell-type selective manner might provide avenues for understanding biological functions of glycans.

  DOI：

  10.1021/ja405189k
• 作为产物：
  描述：

  D-galactosamine hydrochloride 、 4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 水 为溶剂， 以56%的产率得到(2R,3R,4R,5R,6R)-6-(hydroxymethyl)-3-[(4-methoxyphenyl)methylideneamino]oxane-2,4,5-triol
  参考文献：
  名称：

  Profiling of Haemophilus influenzae strain R2866 with carbohydrate-based covalent probes

  摘要：

  在流感嗜血杆菌中使用共价、基于碳水化合物的探针标记蛋白质，可在裂解液和完整细胞中产生独特的靶标谱。

  DOI：

  10.1039/d0ob01971b

文献信息

• Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters
  作者：José A. Carmona、Gonzalo de Gonzalo、Inmaculada Serrano、Ana M. Crespo-Peña、Michal Šimek、David Monge、Rosario Fernández、José M. Lassaletta

  DOI：10.1039/c7ob00308k

  日期：——

  synthesized and their behavior as bifunctional organocatalysts has been tested in the enantioselective nucleophilic addition of formaldehyde tert-butyl hydrazone to aliphatic α-keto esters for the synthesis of tertiary azomethyl alcohols. Using the 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-β-D-glucosamine derived 3,5-bis-(trifluoromethyl)phenyl thiourea the reaction could be accomplished with high yields

  已经合成了一系列过酰基化的氨基糖衍生的硫脲，并且已经在甲醛叔丁基向脂肪族α-酮酯的对映选择性亲核加成反应中合成了偶氮叔甲基醇，对它们作为双功能有机催化剂的行为进行了测试。使用1,3,4,6-四-O-乙酰基-2-氨基-2-脱氧-β - D-葡糖胺衍生的3,5-双-（三氟甲基）苯基硫脲可以高收率地完成反应（ 75–98％）和中等对映选择性（50–64％ee）。随后以单锅方式对芳族和脂族取代的重氮产品进行高产率且无消旋的转化，可直接进入有价值的氮氧基化合物和α-羟基-β-氨基酯。