111956-66-2

Usage

Uses

Used in Organic Synthesis:
(3S,3aR,6R,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-ol is used as a reagent and intermediate in organic synthesis for the production of other chemical compounds. Its unique structure and the presence of the benzyl group make it particularly suitable for reactions involving aromatic chemistry, contributing to the synthesis of various organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (3S,3aR,6R,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-ol may be utilized as a key intermediate in the development of new drugs. Its versatility in organic synthesis allows for the creation of diverse chemical entities that could possess therapeutic properties, potentially leading to the discovery of novel medications.
Used in Chemical Research:
(3S,3aR,6R,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-ol is also used in chemical research to explore new reaction pathways and mechanisms. Its involvement in aromatic chemistry provides a platform for scientists to study and understand complex organic reactions, which can further the knowledge in the field and lead to advancements in synthetic methodologies.

Upstream product

• 100-44-7 benzyl chloride 
• 652-67-5 Isosorbide 
• 100-39-0 benzyl bromide 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 65940-93-4 (6S,3R,3aR,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl acetate 
• 162426-82-6 5-O-acetyl-1,4:3,6-dianhydro-2-O-benzyl-D-glucitol 

Downstream Products

• 183474-38-6 (3R,3aR,6S,6aR)-3-Allyloxy-6-benzyloxy-hexahydro-furo[3,2-b]furan 
• 183556-46-9 Acrylic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester 
• 299433-96-8 C₃₄H₄₆O₈ 
• 299434-03-0 C₃₀H₃₈O₈ 
• 299434-00-7 C₃₂H₄₂O₈ 
• 299434-50-7 C₃₂H₄₂O₁₀ 
• 299434-08-5 C₃₂H₄₂O₁₀ 
• 292148-42-6 2-Methyl-acrylic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester 
• 350010-25-2 2-Methylene-butyric acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester 
• 350010-26-3 2-Phenyl-acrylic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester 
• 433713-54-3 (1R,4S,5R,8R)-4-benzyloxy-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol 
• 399534-53-3 Chloro-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester 
• 352530-47-3 Chloro-acetic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 324027-27-2 (Triphenyl-λ⁵-phosphanylidene)-acetic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 

Relevant academic research and scientific papers

Synthesis of novel chiral imidazolium-based ionic liquids derived from isosorbide and their applications in asymmetric aza Diels-Alder reaction

A novel family of chiral imidazolium-based ionic liquids containing a chiral moiety and a free hydroxyl function has been designed and synthesized using isosorbide as a biorenewable substrate. These chiral ionic liquids were found to catalyze the aza Diels-Alder reaction to give good yields and moderate diastereoselectivities. Chiral ionic liquids are recycled while their efficiency is preserved.

An efficient method for the preparation of Chiral Mosher's acid analogues

A diastereoselective trifluoromethylation of chiral α-keto esters derived from isosorbide with TMSCF3 in the presence of a Lewis-base catalyst gave the corresponding trifluoromethylated α-hydroxy esters in good yields with moderate to high dias

Bio-Based Amides from Renewable Isosorbide by a Direct and Atom-Economic Boric Acid Amidation Methodology

The functionalization of bio-sourced isohexides has proved challenging over the last number of years, especially in polymer and medicinal chemistry. We report herein the synthesis of bio-based amido-isohexides by the known boric acid catalysed amidation reaction. The coupling reaction was successfully performed with aliphatic and aromatic carboxylic acids. The extension of the scope of the reaction to eight Boc-protected amino acids is also described, the products being obtained in moderate to good yields. A preliminary screening of these new potential organocatalysts was carried out for the aldolization of isatin. We describe herein the formation of the amide bond between amines derived from dianhydrohexitols and carboxylic or amino acids mediated by a catalytic quantity of boric acid.

Chiral ionic liquids derived from isosorbide: Synthesis, properties and applications in asymmetric synthesis

A novel class of chiral ammonium and imidazolium-based ionic liquids has been designed and synthesized using isosorbide as a biorenewable substrate. These chiral ionic liquids were found to catalyze the aza Diels-Alder reaction to give good yields and moderate diastereoselectivitives.

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

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

Isomannide and isosorbide as new chiral auxiliaries for the stereoselective synthesis of tertiary α-hydroxy acids

Isomannide and isosorbide are selectively protected to provide new chiral auxiliaries suitable for the preparation of enantiopure tertiary α-hydroxy acids. Diastereoselective additions of organozinc reagents on the derived phenylglyoxylates afford the desired α-hydroxy acids with 60-99% ee after saponification. Both absolute configurations of the α-hydroxy acids can be accessed, by adapted choice of either the starting diol or the protecting group.

Highly diastereoselective 5-hexenyl radical cyclizations with Lewis acids and carbohydrate scaffolds.

[figure: see text] Carbohydrates as removable chiral scaffolds for free radical cyclizations were examined for the first time. This investigation illustrates the utility of two inexpensive carbohydrate derivatives as sources of asymmetry for 5-hexenyl rad

Synthesis of New Diols Derived from Dianhydrohexitols Ethers under Microwave-Assisted Phase Transfer Catalysis

Alkylation of mono-benzylated isosorbide and isomannide was performed under microwave assisted phase transfer catalysis (PTC). A small amount of solvent was necessary to provide good yields (90-96%) within 15 min. In order to minimize the competitive elimination, halide leaving group was changed to tosylate as competitive S(N)2-E2 processes were involved. After removal of benzyl moiety by hydrogenation, a series of new diols from dianhydrohexitols were thus prepared. (C) 2000 Elsevier Science Ltd.

Asymmetric Diels-Alder: Monobenzylated isosorbide and isomannide as highly effective chiral auxiliaries

Lewis acid promoted Diels-Alder reactions of acrylate esters from monobenzylated isosorbide or isomannide and cyclopentadiene provided exclusively endo-adducts with good yields and high diastereoselectivities. The R/S selectivities are quasi total and opposed using either isosorbide or isomannide derivatives.