111956-66-2

Basic information

• Product Name: (3S,3aR,6R,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-ol
• Synonyms: (3S,3aR,6R,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-ol
• CAS NO: 111956-66-2
• Molecular Formula: C13H16O4
• Molecular Weight: 236.268
• Mol File: 111956-66-2.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (3S,3aR,6R,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,3aR,6R,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-ol(111956-66-2)
• EPA Substance Registry System: (3S,3aR,6R,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-ol(111956-66-2)

Safety Data

• Hazardous Substances Data: 111956-66-2(Hazardous Substances Data)

Usage

Description

(3S,3aR,6R,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-ol is a hexahydrofuro[3,2-b]furan-3-ol derivative with a molecular formula of C14H18O3. It is a white solid with a melting point of 115-117°C and features a benzyl group attached to the oxygen atom. (3S,3aR,6R,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-ol is significant in the field of organic chemistry due to its potential applications and reactivity in aromatic chemistry.

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

• 652-67-5 Isosorbide 
• 65940-93-4 (6S,3R,3aR,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl acetate 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 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 
• 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 
• 350010-26-3 2-Phenyl-acrylic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester 

Relevant articles and documents

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.

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.

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