76236-32-3

Basic information

• Product Name: (5S)-5-[(trityloxy)methyl]furan-2(5H)-one
• Synonyms: 2(5H)-furanone, 5-[(triphenylmethoxy)methyl]-, (5S)-
• CAS NO: 76236-32-3
• Molecular Formula: C₂₄H₂₀O₃
• Molecular Weight: 356.4138
• Mol File: 76236-32-3.mol

Chemical Properties

• Boiling Point: 517.6°C at 760 mmHg
• Flash Point: 224.7°C
• Density: 1.183g/cm³
• Vapor Pressure: 8.05E-11mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: (5S)-5-[(trityloxy)methyl]furan-2(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5S)-5-[(trityloxy)methyl]furan-2(5H)-one(76236-32-3)
• EPA Substance Registry System: (5S)-5-[(trityloxy)methyl]furan-2(5H)-one(76236-32-3)

Safety Data

• Hazardous Substances Data: 76236-32-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
(5S)-5-[(trityloxy)methyl]furan-2(5H)-one is used as a building block for the synthesis of complex organic molecules. Its unique structure and the presence of the trityloxy protecting group make it suitable for creating a variety of compounds with specific functionalities and properties.
Used in Chemical Synthesis:
(5S)-5-[(trityloxy)methyl]furan-2(5H)-one is utilized as an intermediate in chemical synthesis processes. The trityloxy group's protective nature allows for selective reactions, enabling the creation of target molecules with greater precision and control over the synthetic pathway.
Used in Research and Development:
(5S)-5-[(trityloxy)methyl]furan-2(5H)-one is employed as a research tool in the field of organic chemistry. Its properties and reactivity can be studied to gain insights into the behavior of similar compounds and to develop new synthetic strategies and methodologies.
Used in Pharmaceutical Industry:
(5S)-5-[(trityloxy)methyl]furan-2(5H)-one may be used as a starting material or intermediate in the development of new pharmaceutical compounds. Its unique structure could potentially be exploited to design novel drugs with specific therapeutic properties.
Used in Material Science:
(5S)-5-[(trityloxy)methyl]furan-2(5H)-one's structural characteristics could also make it a candidate for the development of new materials with specialized properties, such as those with unique optical, electronic, or mechanical characteristics, depending on the final synthesized product.

Upstream product

• 84911-44-4 2,3-O-(thiocarbonyl)-5-O-(triphenylmethyl)-D-ribono-1,4-lactone 
• 36326-38-2 3-<(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>prop-2-enoic acid ethyl ester 
• 78508-93-7 2,3-O-(ethoxymethylene)-D-ribonic acid γ-lactone 
• 78508-93-7 (+)-2,3-O-ethoxymethylene-D-ribonolactone 
• 66601-82-9 methyl (S)-4,5-dihydroxy-4,5-O-isopropylidene-2-pentenoate 
• 5336-08-3 D-Ribono-1,4-lactone 
• 76-83-5 trityl chloride 
• 73968-62-4 (5S)-5-[(trityloxy)methyl]tetrahydro-2-furanone 
• 84911-43-3 (3R,4S,5R)-3,4-dihydroxy-5-(trityloxymethyl)-dihydrofuran-2(3H)-one 
• 34371-14-7 2-deoxy-D-ribonolactone 
• 20603-45-6 3,4-O-Benzylidene-D-(+)-ribonic acid δ-lactone 
• 146918-99-2 3,4-O-(R)-benzylidene-2-deoxy-D-erythro-ribono-1,5-lactone 
• 76236-31-2 (4S)-(+)-2-phenylseleno-4-trityloxymethyl-butan-4-olide 
• 149142-33-6 5-O-trityl-2-deoxy-D-erythro-pentono-1,5-lactone 

Downstream Products

• 157543-30-1 (4R,5S)-4-sec-Butyl-5-trityloxymethyl-dihydro-furan-2-one 
• 76236-34-5 (4S,5S)-4-(3,4,5-Trimethoxy-benzyl)-5-trityloxymethyl-dihydro-furan-2-one 
• 92232-57-0 (3S,4S,5S)-3-Benzo[1,3]dioxol-5-ylmethyl-4-(3,4,5-trimethoxy-benzyl)-5-trityloxymethyl-dihydro-furan-2-one 
• 76236-36-7 (2S,3S,4S)-(+)-3-(3',4',5'-trimethoxybenzyl)-4-piperonyl-1,2,5-pentanetriol 
• 76236-35-6 (3S,4S)-(+)-3-(3,4,5-trimethoxybenzyl)-4-hydroxymethyl-butan-4-olide 
• 72627-52-2 (2S,3S,4S)-(+)-2-piperonyl-3-(3,4,5-trimethoxybenzyl)-4-hydroxymethyl-butan-4-olide 
• 84911-45-5 (S)-4-Methyl-5-trityloxymethyl-dihydro-furan-2-one 
• 81480-31-1 (S)-(-)-4-methyl-5-trityloxymethyl-2(5H)-furanone 
• 53798-51-9 Verrucarinsaeure, α,δ-Dihydroxy-β-methyl-valeriansaeure 
• 313646-43-4 (3R,5S)-3-Trimethylsilanyloxy-5-trityloxymethyl-dihydro-furan-2-one 
• 313646-51-4 (3S,5S)-3-Trimethylsilanyloxy-5-trityloxymethyl-dihydro-furan-2-one 
• 313646-56-9 Acetic acid (2S,3R,5S)-2-methyl-5-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 313646-47-8 (2S,3R,5S)-2-Methyl-5-trityloxymethyl-tetrahydro-furan-3-ol 
• 313646-53-6 (2S,3S,5S)-2-Methyl-5-trityloxymethyl-tetrahydro-furan-3-ol 

Relevant articles and documents

Synthesis of (+)-muscarine from (S)-(-)-5-hydroxymethyl-2(5H)-furanone

(+)-Muscarine has been synthesized from (S)-(-)-5-hydroxy-2(5H)-furanone via rather a long pathway to provide easy access to a wide variety of its analogues. (C) 2000 Published by Elsevier Science Ltd.

Chiral synthesis of (S)-(+)-γ-hydroxymethyl-γ-butyrolactone

S-(+)-γ-hydroxymethyl-γ-butyrolactone has been synthesized from D- ribonolactone as chiral template.

A synthetic route to 3-C-alkyl (or 3-C-phenyl-) 2,3-dideoxy-D-erythro- pentono-1,4-lactones: Intermediates in the synthesis of 2(3H)-furanones

A series of 3-C-alkyl- (and 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono- 1,4-lactones, compounds which are important in the synthesis of modified nucleosides and antibiotic sugars, were synthesized from D-ribonolactone. By a route that proceeded via 5-O-pr

Vitamin C and Isovitamin C Derived Chemistry. 3. Chiral Butenolides via Efficient 2,3-Didehydroxylations of L-Gulono-, D-Mannono-, and D-Ribono-1,4-lactones

Efficient, operationally simple procedures for preparing the chiral butenolides 3a, 4a, 13a,b, and 16a-d from the commercial L-ascorbic acid (L-threo-hex-2-enono-1,4-lactone) and D-isoascorbic acid (D-erythro-hex-2-eno-no-1,4-lactone) are described.The concept centers on the novel NaHSO3-induced regiospecific trans-β-bromo-acetoxy elimination of the readily accessible O-acetylated bromodeoxyaldono-1,4-lactones 10a,b to compounds 13a,b.These, on deacetylation and treatment of the resulting bromohydrins 16a,b with Ag2O, afford the enantiomerically pure epoxides 16c,d and thence, in boiling water, the corresponding diols 3a and 4a.In a similar manner NaHSO3 causes the D-ribono-1,4-lactone-derived bromo acetate mixture 17a,b to undergo elimination to the corresponding butenolides 18a,b, which, on subsequent hydrolysis and chromatographic purification, has given compound 1a in 48percent overall yield.

A Short Synthesis of (S)-5-Hydroxy-2-penten-4-olide from D-Mannitol via 2,3-O-Isopropylidene-D-glyceraldehyde

(S)-5-Hydroxy-2-penten-4-olide (5) was synthesized in three steps starting from D-mannitol bis(acetonide) (1), via D-glyceraldehyde acetonide (2) by Z-selective Wittig reaction, acid-catalyzed lactonization and crystallization with a total yield of 40percent.

ASYMMETRIC TOTAL SYNTHESIS OF NATURAL (-)- AND UNNATURAL (+)-STEGANACIN DETERMINATION OF THE ABSOLUTE CONFIGURATION OF NATURAL ANTITUMOR STEGANACIN

A virtually complete asymmetric control in the synthesis of 2,3-disubstituted butan-4-olide (10) was demonstrated by employing the butenolide (12) as the chiral acceptor for the conjugate 1,4-addition.Highly efficient asymmetric total synthesis of natural (-)- and unnatural (+)-steganacin was accomplished.The absolute stereostructure of natural antitumor steganacin was determined to be 1.

STUDIES ON STRUCTURALLY SIMPLE α,β-BUTENOLIDES-II (-)-(S)-γ-HYDROXYMETHYL-α,β-BUTENOLIDE AND DERIVATIVES FROM D-RIBONOLACTONE EFFICIENT SYNTHESIS OF (-)-RANUNCULIN

A short synthesis of the title compound, 16, from D-ribonolactone is described.Two alternative approaches differing in the timing of the C=C double bond creation are used to prepare some chiral derivatives of 16. (-)-Ranunculin, a glycoside present in Ranunculaceae, has been synthetized for the first time.

SYNTHETIC APPROACHES TOWARD VERRUCARIN A. CHIRAL SYNTHESIS OF (-)-VERRUCARINOLACTONE

(-)-Verrucarinolactone ((2S,3R)-2,5-dihydroxy-3-methylvaleric acid δ-lactone) (4) was synthesized stereoselectively from an optically active butyrolactone ((S)-γ-trityloxymethyl-γ-butyrolactone) (6) as a chiral synthon.

A SHORT SYNTHESYS OF (S)-5-HYDROXYMETHYL-(5H)-FURAN-2-ONE AND DERIVATIVES FROM D-RIBONOLACTONE

We describe a short synthesis of (S)-5-hydroxymethyl-(5H)-furan-2-one and some 5-O-derivatives, which are being used as key starting products for the synthesis of several antileukaemic lignan lactones, from D-ribonolactone.