2,3,4,6-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptose | 71420-09-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptose
• 英文别名: 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptose；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-formyloxan-2-yl]methyl acetate
• CAS: 71420-09-2
• 化学式: C₁₅H₂₀O₁₀
• 分子量: 360.318
• InChiKey: NGGOLVRARHJQLH-AIEDFZFUSA-N

物化性质

• 沸点：
  427.6±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptose 在 吡啶 、 甲醇 、 sodium tetrahydroborate 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 20.33h， 生成 2,6-anhydro-L-glycero-L-galacto-heptitol
  参考文献：
  名称：

  Synthesis studies of structural analogues of tagetitoxin: 2-phosphate

  摘要：

  Synthetic approaches to structural analogues of tagetitoxin (1) are described. The successful route to analogue 3 (X=O) has, as a key step, protection of the cis-vicinal amino alcohol moiety of compound 7 as an N-benzylated cyclic carbamate (9). X-Ray crystallographic analyses of the hydrochloride of compound 7 and of the hydroxyacid 56 are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00327-0
• 作为产物：
  描述：

  6-羰基-1,6-二氢-3,4'-联吡啶-5-甲腈 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.33h， 生成 2,3,4,6-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptose
  参考文献：
  名称：

  Synthesis studies of structural analogues of tagetitoxin: 2-phosphate

  摘要：

  Synthetic approaches to structural analogues of tagetitoxin (1) are described. The successful route to analogue 3 (X=O) has, as a key step, protection of the cis-vicinal amino alcohol moiety of compound 7 as an N-benzylated cyclic carbamate (9). X-Ray crystallographic analyses of the hydrochloride of compound 7 and of the hydroxyacid 56 are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00327-0

文献信息

• Synthesis of 4,8-anhydro-2,3-dideoxy-d-galacto- and -d-gluco-non-3-enose dimethyl acetal and their use as new probes for determining by 1H-n.m.r. spectroscopy the steric course of protonation by glycoside hydrolases
  作者：Hanz Fritz、Jochen Lehmann、Markus Schmidt-Schuchardt、Wolfgang Weiser

  DOI：10.1016/0008-6215(91)84092-s

  日期：1991.9

  by multistep syntheses. Addition of water to the enolic double bonds of both compounds was catalyzed only by the corresponding enzymes β- d -galactosidase from Escherichia coli , α- d -galactosidase from green coffee beans, and β- d -glucosidase from sweet almonds, α- d -glucosidase from yeast. The enzymic hydration of 2 , performed in D 2 O to analyze the steric course of the addition, gave 2,3-dideoxy-α-

  摘要通过多步合成法制备了标题非蔗糖衍生物2（d-galacto）和4-（d-葡萄糖）。仅通过来自大肠杆菌的相应酶β-d-半乳糖苷酶，来自生咖啡豆的α-d-半乳糖苷酶和来自甜杏仁的β-d-葡萄糖苷酶，α-d才将水加至这两种化合物的烯醇双键中。 -酵母中的葡萄糖苷酶。在D 2 O中进行2的酶促水合以分析加成反应的空间过程，得到2,3-二脱氧-α-d-半乳糖-（3- 2 H）-壬基-4-纤维素二甲基乙缩醛（5） ，当水解时，提供了以螺烷16和17为主要产物（85％）和稠环系统18和19为次要成分（15％）的平衡混合物。酶促水合产物的硼氢化物还原得到两种差向异构体14和15的可分离混合物，可在酸性甲醇中于62°转化8小时，分别转化为20和22。刚性的双环系统允许轻松地将单氘C-3上的构型指定为（S），从而可以确定酶催化起始步骤的空间过程，即底物中烯醇双键的氘化用过的。
• New and general synthesis of β-C-glycosylformaldehydes from easily available β-C-glycosylpropanones
  作者：Stéphanie Norsikian、Jennifer Zeitouni、Stéphanie Rat、Sylvie Gérard、André Lubineau

  DOI：10.1016/j.carres.2007.09.002

  日期：2007.12

  A highly effective method for the introduction of a formyl group at the anomeric position of pyranosides was developed via enolisation Of beta-C-D-glycopyranosylpropan-2-one using thermodynamic conditions then oxidative cleavage of the more substituted double bond. This sequence affords the desired aldehydes that are conveniently protected as aminals for purification and storage and easily regenerated using Dowex resin H+. In this paper, the syntheses of nine differently protected aldehydes derived from D-glucose, D-galactose. lactose and N-acetyl-D-glucosamine are presented. Our strategy proved to be very efficient in most cases excepted in the D-mannose series. (C) 2007 Elsevier Ltd. All rights reserved.