83780-62-5

Upstream product

• 83780-60-3 (2R)-2-(oxan-2-yloxy)propan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 110-87-2 3,4-dihydro-2H-pyran 
• 103775-61-7 (R)-2-hydroxypropyl 4-methylbenzenesulfonate 
• 32464-98-5 (2S)-2-hydroxypropyl 4-methylbenzenesulfonate 
• 3539-39-7 (S)-(-)-2-(tetrahydropyranyloxy)propanol 
• 160616-60-4 2-methylpropyl (R)-2-(tetrahydropyran-2-yloxy)propanoate 
• 3539-40-0 Ethyl (S)-(-)-2-tetrahydropyran-2-yloxypropionate 

Downstream Products

• 1018960-02-5 C₂₀H₂₃BrO₃ 
• 143331-41-3 (2S,12S)-(-)-2,12-bis(tetrahydropyranyloxy)-7-trityl-7-aza-4,10-dioxatridecane 

Relevant academic research and scientific papers

Stable hydrazone-linked chiral covalent organic frameworks: Synthesis, modi?cation, and chiral signal inversion from monomers

The designed synthesis of chiral covalent organic frameworks (COFs) featuring intriguing properties is fairly scant and remains a daunting synthetic challenge. Here we develop a de novo synthesis of an enantiomeric pair of 2D hydroxyl-functionalized hydra

Molecular tectonics: Homochiral 3D cuboid coordination networks based on enantiomerically pure organic tectons and ZnSiF6

Upon combining enantiomerically pure bis-monodentate organic tectons with ZnSiF6, homochiral 3D cuboid architectures displaying chiral channels are formed.

Constitutionally asymmetric and chiral [2]pseudorotaxanes

The self-assembly and characterization of a range of chiral pseudorotaxanes has been explored using chiroptical methods. The syntheses of (i) constitutionally asymmetric acyclic hydroquinone-containing polyethers and (ii) optically active hydroquinone-containing acyclic polyethers, bearing pairs of methyl or isobutyl groups related to each other in a C2-symmetric manner within the polyether backbone, are described. The combination of (i) the tetracationic cyclophane cyclobis(paraquat-p-phenylene) tetrakis(hexafluorophosphate), possessing a π-electron deficient cavity, and (ii) the linear noncentrosymmetric acyclic polyethers produces [2]pseudorotaxanes that have been characterized by 1H NMR, UV/vis and circular dichroism (CD) spectroscopies in solution and by X-ray crystallography in the solid state. The introduction of constitutional asymmetry or chirality gives rise to a number of different geometries for the [2]pseudorotaxanes in both the solution and solid states. In particular, CD-spectroscopic measurements on the optically active [2]pseudorotaxanes have shown that-depending on the positions of the C2 symmetrically related chiral centers in the polyether chains with respect to the hydroquinone rings - the chirality present in the π-electron rich threadlike guest can induce chirality that is associated with the supramolecular structure as a whole, resulting in a chiral charge-transfer transition involving not only the π-donors in the chiral guests but also the π-acceptors in the achiral host.

SYNTHESIS OF ENANTIOMERIC N-(2-PHOSPHONOMETHOXYPROPYL) DERIVATIVES OF PURINE AND PYRIMIDINE BASES. I. THE STEPWISE APPROACH

The (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases (PMP derivatives) exhibit very high activity against retroviruses.This paper describes the synthesis of enantiomeric 9-(2-phosphonomethoxypropyl)adenines (I and XXVII), 9-(2-phosphonomethoxypropyl)-2,6-diaminopurines (II and XXXI), 9-(2-phosphonomethoxypropyl)guanines (III and XXIX) and 1-(R)-(2-phosphonomethoxypropyl)cytosine (XIX) by alkylation of N-protected N-(2-hydroxypropyl) derivatives of the corresponding bases with bis(2-propyl) p-toluenesulfonyloxymethylphosphonate (X), followed by stepwise N- and O-deprotection of the intermediates.The key intermediates, N-(2-hydropxypropyl) derivatives IX and XXV, were obtained by alkylation of the appropriate heterocyclic base with (R)- or (S)-2-(2-tetrahydropyranyloxy)propyl p-toluenesulfonate (VII or XXIII) ans acid hydrolysis of the resulting N- derivatives VIII and XXII.The chiral synthons were prepared by tosylation of (R)- or (S)-2-(2-tetrahydropyranyloxy)propanol (VI or XXI) available by reduction of enantiomeric alkyl 2-O-tetrahydropyranyllactates V and XXI with sodium bis(2-methoxyethyoxy)aluminum hydride.This approach was used for the synthsis of cytosine, adenine and 2,6-diaminopurine derivatives, while compounds derived from guanine were prepared by hydrolysis of 2-amino-6-chloropurine intermediates.Cytosine derivative IXe was also synthesized by alkylation of 4-methoxy-2-pyrimidone followed by ammonolysis of the intermediate IXf.

New Symmetrical Chiral Dibenzyl- and Diphenyl-Substituted Diamido-, Dithionoamido-, Diaza-, and Azapyridino-18-crown-6 Ligands

Eleven new chiral macrocycles (1-11, see Figure 1) of the pyridino-18-crown-6 type have been prepared.Nine diazapyridino-crown ligands contain two amide (1, R = benzyl; 4, R = phenyl), two N-methylamide (7, R = phenyl), two thionoamide (2, R = benzyl; 5,

The Synthesis of Chiral Dimethyl Substituted Macrocyclic Polyether-Diester Ligands (1)

A new series of chiral macrocyclic polyether-diester ligands has been prepared from four chiral dimethyl substituted tetraethylene glycols (15a,b,16,17) and 2,6-pyridinecarbonyl chloride (products 5a-7), diglycolyl chloride (products (8-10), thiadiglycolyl chloride (product 11), 2,5-furandicarbonyl chloride (product 12), 4-chloro-2,6-pyridinedicarbonyl chloride (product 13), and 4-methoxy-2,6-pyridinedicarbonyl chloride (product 14).The chiral dimethyl substituted tetraethylene glycols (15a-17) were prepared from ethyl(S)-lactate.