97506-01-9

Basic information

• Product Name: (3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione
• Synonyms: (3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione
• CAS NO: 97506-01-9
• Molecular Weight: 312.322
• Mol File: 97506-01-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione(97506-01-9)
• EPA Substance Registry System: (3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione(97506-01-9)

Safety Data

• Hazardous Substances Data: 97506-01-9(Hazardous Substances Data)

Usage

Description

(3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione is a chemical compound with the molecular formula C18H16O6. It is a derivative of furandione, also known as maleic anhydride, and is commonly used in the field of organic synthesis. (3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione is characterized by two benzyl groups attached to the oxygen atoms in the 3 and 4 positions, resulting in a cyclic structure with a furan backbone. It has potential applications in the production of pharmaceuticals, agrochemicals, and advanced materials due to its versatile reactivity and unique structure. Additionally, it has been studied for its potential use in the development of new catalysts and organic reactions.

Uses

Used in Pharmaceutical Industry:
(3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione is used as an intermediate in the synthesis of various pharmaceuticals for its versatile reactivity and unique structure.
Used in Agrochemical Industry:
(3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione is used as a building block in the development of agrochemicals, contributing to the creation of effective and novel products.
Used in Advanced Materials:
(3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione is used as a key component in the production of advanced materials, taking advantage of its unique cyclic structure and reactivity.
Used in Catalyst Development:
(3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione is used as a potential candidate in the development of new catalysts, due to its ability to participate in various organic reactions.
Used in Organic Reaction Research:
(3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione is used in the study and development of new organic reactions, given its potential to facilitate novel synthetic pathways.

Upstream product

• 138794-81-7 (2R,3R)-2,3-bis(benzyloxy)tartaric acid 
• 87-69-4 L-Tartaric acid 
• 98-88-4 benzoyl chloride 
• 100-39-0 benzyl bromide 
• 77312-71-1 diethyl (2R,3R)-2,3-bis(benzyloxy)butane-1,4-dioate 

Downstream Products

• 127299-55-2 (3R,4R)-3,4-bis(benzyloxy)pyrrolidine-2,5-dione 
• 1337525-30-0 (2R,3R)-2,3-bis(benzoyloxy)succinic acid mono-((R)-2-isopropyl-2,3-dimethyl-4-oxo-imidazolidin-1-yl) ester 
• 1337525-29-7 (2R,3R)-2,3-bis(benzoyloxy)succinic acid mono-((S)-2-isopropyl-2,3-dimethyl-4-oxo-imidazolidin-1-yl) ester 
• 321566-90-9 (3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione 
• 1354635-09-8 (3R,4R)-1-benzyl-3,4-bis(benzyloxy)pyrrolidine-2,5-dione 
• 1401240-92-3 (S)-2-(benzyloxy)-8-isopropyl-7-methyl-6,7-dihydroindolizin-3(5H)-one 
• 1401240-88-7 (1S,2S,3R,7S,8aR)-1,2-bis(benzyloxy)-3-butyl-8,8-difluoro-7-methyloctahydroindolizine 
• 1401240-91-2 (S)-2-(benzyloxy)-8-butyl-7-methyl-6,7-dihydroindolizin-3(5H)-one 
• 1401240-87-6 (1S,2S,3R,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine 
• 1401240-89-8 (1S,2S,3S,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine 
• 1401240-85-4 (1S,2R,7S,8aR)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one 
• 1401240-86-5 (1S,2R,7S,8aS)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one 

Relevant articles and documents

Diastereoselective ritter-like reaction on cyclic trifluoromethylated N,O-acetals derived from L-tartaric acid

Despite the presence of the highly electron-withdrawing fluorinated substituent, cyclic α-trifluoromethylated N-acyliminium ions were successfully generated from fluorinated O-acetyl-N,O-acetal L-tartaric acid derivatives. The addition of nitriles on these intermediates occurred with high to excellent syn diastereoselectivity and led, in most cases, to oxazolines and amides as single diastereomers. The diastereoselectivity of the addition and the nature of the reaction product depend on the substituents on the hydroxyl groups of the tartaric acid scaffold. This methodology gave access to enantiopure, highly functionalized 5-(trifluoromethyl)pyrrolidin-2-one derivatives, bearing the fluorinated substituent on a tetrasubstituted carbon.

Inexpensive, multigram-scale preparation of an enantiopure cyclic nitrone via resolution at the hydroxylamine stage

The reduction of the chiral, racemic nitrone MiPNO provides a secondary hydroxylamine. Its O-acylation with O,O'-dibenzoyl-l-tartaric acid anhydride gives two diastereomers, that can be easily separated by selective dissolution in orthogonal solvents. The recovery of the enantiopure nitrone is then carried out in a single step. The process allows the straightforward isolation of (R) and (S)-MiPNO in 57% and 38% yield, respectively, from rac-MiPNO.

Acyliminium cyclization of several chiral N-alkenylsuccinimide derivatives

The acyliminium intermediate derived from (3R,4R)-N-(3-butenyl)-3,4-bis(benzyloxy)succinimide cyclized to give (8aS)- and (8aR)-hexahydro-3(2H)-indolidinone derivatives. On the other hand, those derived from N-3-hexenyl derivatives afforded (8aS)-hexahydr