183624-93-3

Upstream product

• 100-44-7 benzyl chloride 
• 641-74-7 1,4:3,6-dianhydro-D-mannitol 
• 100-39-0 benzyl bromide 

Downstream Products

• 183812-62-6 Acrylic acid (3R,3aR,6R,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester 
• 289033-88-1 ([(3R,3aS,6R,6aR)-6-(benzyloxy)perhydro[3,2-b]furan-3-yl]oxy)trimethylsilane 
• 299434-13-2 C₃₂H₄₂O₈ 
• 299434-10-9 C₃₄H₄₆O₈ 
• 299434-16-5 C₃₀H₃₈O₈ 
• 299434-19-8 C₃₀H₃₈O₉ 
• 299434-50-7 C₃₂H₄₂O₁₀ 
• 433713-62-3 [4-(1R,4R,5R,8R)-8-benzyloxy-2,6-dioxabicyclo[3.3.0]octane]-(2-oxo-2-phenyl)-ethanoate 
• 433713-56-5 (1R,4R,5R,8R)-8-benzyloxy-4-methoxy-2,6-dioxabicyclo[3.3.0]octanol 
• 634610-79-0 2-O-benzyl-5-O-(4'-nitrophenyl)-1,4:3,6-dianhydro-D-mannitole 
• 745794-56-3 2-O-benzyl-5-O-(3'-iodophenyl)-1,4:3,6-dianhydro-D-mannitole 
• 292148-40-4 2-Methyl-acrylic acid (3R,3aR,6R,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester 
• 634610-81-4 2-O-benzyl-5-O-(4'-iodophenyl)-1,4:3,6-dianhydro-D-mannitole 
• 745794-49-4 4-((3R,3aR,6R,6aR)-6-Benzyloxy-hexahydro-furo[3,2-b]furan-3-yloxy)-phenylamine 

Relevant academic research and scientific papers

Exploiting π shielding interactions in a η6 arene-complexed chiral auxiliary

The origin of asymmetric induction in a chiral auxiliary derived from isomannide was probed using a series of η6 arene chromium carbonyl complexes. Diastereoselectivity as high as 99% was attainable, and subsequent spectroscopic analysis shed light on the role of π-π interactions. (C) 2000 Elsevier Science Ltd.

ETHER COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS

Compounds, methods of use, and processes for making inhibitors of complement Factor D comprising Formula I, or a pharmaceutically acceptable salt or composition thereof wherein R12 or R13 on the A group is an ether substituent (R32) are provided. The inhibitors described herein target Factor D and inhibit or regulate the complement cascade. The inhibitors of Factor D described herein reduce the excessive activation of complement.

Nucleophilic Aromatic Substitution (SNAr) as an Approach to Challenging Carbohydrate-Aryl Ethers

A general and practical route to carbohydrate-aryl ethers by nucleophilic aromatic substitution (SNAr) is reported. Upon treatment with KHMDS, C-O bond formation occurs between carbohydrate alcohols and a diverse range of fluorinated (hetero)ar

Synthesis of novel chiral monophosphine ligands derived from isomannide and isosorbide. Application to enantioselective hydrogenation of olefins

A new class of monophosphine ligands has been prepared from natural chirality renewable source, 1,4:3,6-dianhydrohexitol compounds, via a nucleophilic substitution process, or a hydrophosphination reaction involving microwave activation. These ligands have been evaluated for the rhodium-catalyzed enantioselective hydrogenation of olefins giving good conversion and enantioselectivity up to 95% and 96% ee, respectively.

Novel peptide mimetics based on N-Protected amino acids derived from isomannide as potential inhibitors of NS3 serine protease of hepatitis C virus

Abstract: Hepatitis C virus (HCV) is among the most important flaviviruses. It has a serine protease which is important for viral replication and this enzyme constitutes a suitable target for new anti-retroviral drugs. Herein we disclose a series of amide and ester peptide mimetic inhibitors of serine proteases, all of them obtained via coupling reactions of isomannide derivatives with N-protected amino acids. The arginine derivative 19 showed 45% of inhibition of NS3/4A serine protease at 100 μM and molecular modeling studies had shown that 19 interacted with the active site of this enzyme.

CHIRAL COMPOUNDS, LIQUID CRYSTAL COMPOSITIONS AND POLYMER NETWORKS DERIVED THEREFROM

Isomannide-based compounds having chiral properties are provided, in addition to liquid crystal compositions and polymer networks derived therefrom.

Exploiting π shielding interactions of η6 arene chromium (0) complexes: New auxiliaries derived from the biogenic chiral pool

A family of highly selective chiral auxiliaries containing arene chromium (0) complexes has been prepared using biogenic precursors from the chiral pool. The systems, derived from isomannide, prolinol, and xylofuranose were applied to the asymmetric Diels-Alder reaction of derived acrylate esters. Factors influencing stereoselectivity with the auxiliaries have been investigated and delineated including the impact of mixed ligands on the chromium (0) complex. Under optimal conditions, the auxiliaries give >95% e.e. and 98:2 exo:endo ratio in cycloaddition with cyclopentadiene.

Asymmetric Horner-Wadsworth-Emmons reaction utilizing isomannide and isosorbide derivatives as chiral auxiliaries

The diastereoselective Horner-Wadsworth-Emmons reaction of chiral phosphonates with σ-symmetric 4-tert-butylcyclohexanone and 4-phenylcyclohexanone was investigated by employing isomannide and isosorbide derivatives as chiral auxiliaries. α-Fluoro-α,β-uns

Synthesis of dianhydrohexitole-based benzamidines as factor xa inhibitors using cross couplings, phenyl ether and amidine formations as key steps

Starting with isosorbide or isomannide several dianhydrohexitole-based benzamidines were synthesized as potential factor Xa inhibitors. The key steps for the synthesis of the bisbenzamidines were nucleophilic aromatic substitutions and Mitsunobu reactions

Aldehyde-alkene cyclizations via O-stannyl ketyl radicals using sugars as chiral auxiliaries

This investigation illustrates the utility of two inexpensive carbohydrate derivatives as sources of asymmetry for aldehyde-alkene radical cyclizations. Diastereomeric ratios as high as 9:1 were achieved with an ester-appended (+)-isosorbide and 100:1 for