(4R,5R)-4-((R)-1-hydroxy-2,2-dimethoxyethyl)-2,2-dimethyl-1,3-dioxan-5-ol | 875903-74-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-4-((R)-1-hydroxy-2,2-dimethoxyethyl)-2,2-dimethyl-1,3-dioxan-5-ol
• 英文别名: (4R,5R)-4-[(1R)-1-hydroxy-2,2-dimethoxyethyl]-2,2-dimethyl-1,3-dioxan-5-ol
• CAS: 875903-74-5
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: NWLBTQNQZGAJLS-BWZBUEFSSA-N

物化性质

• 沸点：
  365.2±37.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-((R)-1-hydroxy-2,2-dimethoxyethyl)-2,2-dimethyl-1,3-dioxan-5-ol 在 Dowex 50W₂-100 作用下， 以 水 为溶剂， 反应 6.5h， 生成 D-核糖
  参考文献：
  名称：

  Dihydroxyacetone Variants in the Organocatalytic Construction of Carbohydrates:  Mimicking Tagatose and Fuculose Aldolases

  摘要：

  Dihydroxyacetone variants have been explored as donors in organocatalytic aldol reactions with various aldehyde and ketone acceptors. The protected form of dihydroxyacetone that was chosen for in-depth study was 2,2-dimethyl-1,3-dioxan-5-one, 1. Among the catalysts surveyed here, proline proved to be superior in terms of yield and stereoselectivities in the construction of various carbohydrate scaffolds. In a fashion analogous to aldolase enzymes, the de novo preparation of L-ribulose, L-lyxose, D-ribose, D-tagatose, 1-amino-1-deoxy-D-lyxitol, and other carbohydrates was accomplished via the use of 1 and proline. In reactions using 2,2-dimethyl-1,3-dioxan-5-one 1 as a donor, (S)-proline can be used as a functional mimic of tagatose aldolase, whereas (R)-proline can be regarded as an organocatalytic mimic of fuculose aldolase.

  DOI：

  10.1021/jo0602017
• 作为产物：
  描述：

  2,2-二甲基-1,3-二恶烷-5-酮 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 L-脯氨酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.0h， 生成 (4R,5R)-4-((R)-1-hydroxy-2,2-dimethoxyethyl)-2,2-dimethyl-1,3-dioxan-5-ol
  参考文献：
  名称：

  Dihydroxyacetone Variants in the Organocatalytic Construction of Carbohydrates:  Mimicking Tagatose and Fuculose Aldolases

  摘要：

  Dihydroxyacetone variants have been explored as donors in organocatalytic aldol reactions with various aldehyde and ketone acceptors. The protected form of dihydroxyacetone that was chosen for in-depth study was 2,2-dimethyl-1,3-dioxan-5-one, 1. Among the catalysts surveyed here, proline proved to be superior in terms of yield and stereoselectivities in the construction of various carbohydrate scaffolds. In a fashion analogous to aldolase enzymes, the de novo preparation of L-ribulose, L-lyxose, D-ribose, D-tagatose, 1-amino-1-deoxy-D-lyxitol, and other carbohydrates was accomplished via the use of 1 and proline. In reactions using 2,2-dimethyl-1,3-dioxan-5-one 1 as a donor, (S)-proline can be used as a functional mimic of tagatose aldolase, whereas (R)-proline can be regarded as an organocatalytic mimic of fuculose aldolase.

  DOI：

  10.1021/jo0602017

文献信息

• Total Synthesis and Immunological Evaluation of the Tri-<scp>d</scp>-<i>glycero</i>-<scp>d</scp>-<i>manno</i>-heptose Antigen of the Lipopolysaccharide as a Vaccine Candidate against <i>Helicobacter pylori</i>
  作者：Junchang Wang、Yiyue Zhang、Yirong Zhu、Junru Liu、Yan Chen、Xin Cao、You Yang

  DOI：10.1021/acs.orglett.0c03105

  日期：2020.11.20

  emerging, no effective vaccine is available to prevent H. pylori infections. Here, we describe the total synthesis of the unique α-(1→3)-linked tri-d-glycero-d-manno-heptose antigen from the lipopolysaccharide of H. pylori serogroups O3 and O6 and strains MO19, D2, D4, and D5 based on de novo synthesis of the differentially protected d-glycero-d-manno-heptosyl building blocks. Immunization of mice with

  幽门螺杆菌是慢性胃炎、消化性溃疡和胃癌的最常见原因，感染了世界上大约一半的人口。尽管基于抗生素的联合疗法的缺点正在显现，但没有有效的疫苗可用于预防幽门螺杆菌感染。在这里，我们描述了独特的α-（1→3） -连接的三-的全合成d -甘油基- d -甘露-heptose抗原从脂多糖幽门螺杆菌血清群O3和O6和菌株MO19，D2，D4，和 D5 基于差异保护的d -甘油- d - 的从头合成甘露糖-庚糖基积木。用半合成糖缀合物对小鼠进行免疫接种引发了非常强大的 T 细胞依赖性抗原特异性免疫反应，导致 IgG1 和 IgG2b 保护性抗体同种型的滴度非常高。免疫后血清识别幽门螺杆菌NCTC 11637 并与完整细菌的表面强烈结合。
• Direct asymmetric organocatalytic de novo synthesis of carbohydrates
  作者：Christoph Grondal、Dieter Enders

  DOI：10.1016/j.tet.2005.09.060

  日期：2006.1

  A biomimetic organocatalytic asymmetric synthesis of carbohydrates can be accomplished by a proline catalyzed aldol reaction with the dihydroxyacetone equivalent 2,2-dimethyl-1,3-dioxan-5-one and various aldehydes. The biomimetic C3+Cn strategy directly generates selectively protected carbohydrates in one step, which can be easily deprotected. Additionally, the stereoselective reduction of the keto

  碳水化合物的仿生有机催化不对称合成可以通过脯氨酸催化的羟醛反应与二羟基丙酮当量的2,2-二甲基-1,3-二恶烷-5-酮和各种醛反应来完成。仿生C 3 + C n策略可在一个步骤中直接生成选择性保护的碳水化合物，可以很容易地对其进行脱保护。另外，酮基功能的立体选择性降低允许直接进入不同的醛糖。
• Stereodivergent Synthesis of d,d- and l,l-glycero-β-allo-Heptopyranoses on a Dioxanone Scaffold
  作者：Marek Majewski、Nagarjuna Palyam、Izabella Niewczas

  DOI：10.1055/s-0032-1290461

  日期：——

  We report a stereodivergent synthesis of both enantiomers of glycero-allo-heptose from 2,2-dimethyl-1,3-dioxan-5-one, a readily available nonchiral scaffold, and from two different synthetic equivalents of glyoxal: dimethoxyacetaldehyde and 1,3-dithiane-2-carboxaldehyde. The short synthetic sequence involves first a proline-mediated, and then a lithium enolate mediated aldol reaction at the alpha-and alpha'-positions of the dioxanone ring, respectively, and demonstrates the complementary nature of organocatalysis and metal enolate based methods.
• Dihydroxyacetone Variants in the Organocatalytic Construction of Carbohydrates:  Mimicking Tagatose and Fuculose Aldolases
  作者：Jeff T. Suri、Susumu Mitsumori、Klaus Albertshofer、Fujie Tanaka、Carlos F. Barbas

  DOI：10.1021/jo0602017

  日期：2006.5.1

  Dihydroxyacetone variants have been explored as donors in organocatalytic aldol reactions with various aldehyde and ketone acceptors. The protected form of dihydroxyacetone that was chosen for in-depth study was 2,2-dimethyl-1,3-dioxan-5-one, 1. Among the catalysts surveyed here, proline proved to be superior in terms of yield and stereoselectivities in the construction of various carbohydrate scaffolds. In a fashion analogous to aldolase enzymes, the de novo preparation of L-ribulose, L-lyxose, D-ribose, D-tagatose, 1-amino-1-deoxy-D-lyxitol, and other carbohydrates was accomplished via the use of 1 and proline. In reactions using 2,2-dimethyl-1,3-dioxan-5-one 1 as a donor, (S)-proline can be used as a functional mimic of tagatose aldolase, whereas (R)-proline can be regarded as an organocatalytic mimic of fuculose aldolase.