78185-08-7

Basic information

• Product Name: (4R,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one
• Synonyms: (4R,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one
• CAS NO: 78185-08-7
• Molecular Weight: 132.116
• Mol File: 78185-08-7.mol

Chemical Properties

• CAS DataBase Reference: (4R,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one(78185-08-7)
• EPA Substance Registry System: (4R,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one(78185-08-7)

Safety Data

• Hazardous Substances Data: 78185-08-7(Hazardous Substances Data)

Upstream product

• 106183-54-4 tert-butyl (4R)-4,5-O-isopropylidene-3,4,5-trihydroxypentanoate 
• 104578-83-8 3-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid methyl ester 
• 158976-92-2 1,3-dibenzyloxy-2-propyl-diazoacetate 
• 102386-14-1 N,N-diisopropyl-3-hydroxyl-4-pentenamide 
• 5736-03-8 O,O'-isopropylidene D-glycerinaldehyde 
• 74262-77-4 methyl (4R)-4,5-O-isopropylidene-3,4,5-trihydroxypentanoate 
• 78138-85-9 2-bromo-2-deoxy-D-xylono-1,4-lactone 

Downstream Products

• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 58879-34-8 (S)-5-tosyloxypentan-4-olide 
• 105122-15-4 (5S)-5-(tert-butyldimethylsilanyloxymethyl)-5H-furan-2-one 
• 106183-58-8 5-tert-butyldimethylsilyl ether of (4R,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one 
• 106183-57-7 5-tert-butyldimethylsilyl ether of (4S,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one 
• 106183-56-6 bis-tert-butyldimethylsilyl ether of (4R,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one 
• 83159-91-5 3,5-di-O-(tert-butyldimethylsilyl)-2-deoxy-D-ribono-1,4-lactone 
• 78508-96-0 (5S)-5-(hydroxymethyl)-5H-furan-2-one 

Relevant articles and documents

Stereospecific 1,2-Silyl Shift in a Cationic Rearrangement with Retention of Configuration at the Migration Origin

Mitsunobu reaction on the hydroxy acids 5 and 10 stereospecifically gave the lactones 7 and 4, respectively, with retention of configuration at C-4.

Stereocontrol in organic synthesis using silicon-containing compounds. Syntheses of (±)-2-deoxyribonolactone and (±)-arabonolactone

Samarium iodide reacts with methyl (Z)-3-dimethyl(4-methylphenyl)silylprop-2-enoate 5b to give dimethyl (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]hexane-1,6-dioate 8b with high stereoselectivity. This meso diester can be converted into (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]pentan-5-olide 16 by Dieckmann cyclisation, demethoxycarbonylation and Baeyer-Villiger reaction. Silyl-to-hydroxy conversion and relactonisation gave (±)-deoxyribonolactone, and anti-selective enolate hydroxylation followed by silyl-to-hydroxy conversion gave (±)-arabonolactone. An attempt to synthesise sugars with the relative configuration (3RS,4RS) was thwarted by an unprecedented retention of configuration at the migration origin in the cationic rearrangement of (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]-5-hydroxypentanoic acid 28 to (3RS,4SR)-3,5-bis[dimethyl(4-methylphenyl)silyl]pentan-1,4-olide 30.

SYNTHESIS OF 2-DEOXYXYLOLACTONE FROM GLYCEROL DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE CARBON-HYDROGEN INSERTION REACTIONS

diazodecomposition of 1,3-dialkoxy-2-propyl diazoacetates catalyzed by chiral dirhodium(II) carboxamides results in highly enantioselective and diastereoseelctive carbon-hydrogen insertion which forms 3,5-dialkyl 2-deoxyxylolactones in up to 98percent enantiomeric excess.

REACTION OF METHYL DIAZOACETATE WITH 2,3 O-ISOPROPYLIDENE-D-GLYCERALDEHYDE. STEREOSELECTIVITY IN THE SYNTHESIS OF 2-DEOXY-D-ALDONATES AND 2-DEOXY-γ,D-ALDONOLACTONES.

The reaction of 2,3-O-isopropylidene-D-glyceraldehyde with diazoacetates are revised.In the absence of catalyst, the methyl (3S,4R) and (3R,4R)-4,5-O-isopropylidene-2-diazo-3,4,5-trihydroxypentanoate (4a and 4b) were the new and main products in a high stereoselective reaction (84:16).These products were easily converted into the corresponding 2-deoxy-3-ulosonates (3), 2-deoxy-aldonates (6,7 and 8) and 2-deoxy-γ,D-aldonolactones (9 and 10).

A NEW SYNTHESIS OF (S)-5-HYDROXYMETHYL-2(5H)-FURANONE - A MULTIPURPOSE SYNTHON

The multipurpose chiral synthons (S)-5-hydroxymethyl-2(5H)-furanone and its tert-butyldimethylsilyl ether were synthesized from 2,3-O-isopropylidene-D-glyceraldehyde in four or five stages through derivatives of 2-deoxy-D-ribonolactone.

EFFICIENT SYNTHESIS OF (S)-5-HYDROXYMETHYL-5(H)-FURAN-2-ONE FROM D-MANNITOL

Chiral synthons - (S)-5-hydroxymethyl-5(H)-furan-2-one and its t-butyldimethylsilyl ether - were synthsized from D-mannitol in 6-7 steps via 2-desoxy-D-ribonolactone derivatives.

Preparation of Some 2,3-Dideoxylactones by an Unusual Catalytic Hydrogenolysis

Hydrogenolysis of 2-bromo-2-deoxyaldono-1,4-lactones in ethanol solution with palladium as catalyst gives good yields of the corresponding 2,3-dideoxylactones with removal of not only the bromine atom but also the C-3 hydroxy group.

Stereoselective Oxylactonization. Preparation of 2-Deoxy-DL-ribono-1,4-lactone Derivatives from 3-Silyloxy-4-alkenamides

The oxylactonization of 3-silyloxy-4-alkenamides proceeds stereoselectively by treatment with m-chloroperbenzoic acid to give the corresponding 2-deoxy-DL-ribono-1,4-lactone derivatives.

THE CHEMISTRY OF O-SILYLATED KETENE ACETALS; DIASTEREOSELECTIVE ALDOL REACTION OF 2,3-O-ISOPROPYLIDENE-D (AND L)-GLYCERALDEHYDES LEADING TO 2-DEOXY-D (AND L)-RIBOSES

Diastereoselective carbon-carbon bond forming reaction of 2,3-O-isopropylidene-D (and L)-glyceraldehydes (D and L-2) with ketene silyl acetals (1a,b) occured in acetonitrile under mild conditions to give the corresponding anti-β-siloxyesters (D and L-3a) as major products, which could be converted through a few additional steps to 2-deoxy-D (and L)-riboses.