94944-62-4

Usage

General Description

1,3-Dioxolane-4-propanenitrile, 2,2-dimethyl-, (4S)-, also known as Dioxolane, is a chemical compound with the molecular formula C7H11NO2. It is a clear, colorless liquid and is commonly used as a solvent in various industrial and laboratory processes. It is also used in the production of pharmaceuticals, pesticides, and other organic compounds. The (4S) in the chemical name refers to the stereochemistry of the molecule, indicating that it has a specific three-dimensional arrangement of atoms. 1,3-DIOXOLANE-4-PROPANENITRILE, 2,2-DIMETHYL-, (4S)- is flammable and should be handled with care, following proper safety precautions in its use and storage.

InChI:InChI=1/C8H13NO2/c1-8(2)10-6-7(11-8)4-3-5-9/h7H,3-4,6H2,1-2H3/t7-/m0/s1

Upstream product

• 42890-78-8 (S)-(-)-isopropylidenedioxybutyl bromide 
• 143-33-9 sodium cyanide 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 32233-43-5 2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol 
• 39029-45-3 3-(2,2-dimethyl-1,3-dioxolan-4-yl)acrylonitrile 
• 94992-56-0 (S)-1,2-O-isopropylidene-4-O-<(4-methylphenyl)sulfonyl>-1,2,4-butanetriol 

Downstream Products

• 94944-63-5 (S)-1,2-O-isopropylidene-5-amino-1,2-pentanediol 
• 143900-44-1 tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate 
• 94944-69-1 (S)-3-hydroxypiperidine-N-carboxylate benzyl ester 
• 24211-55-0 (S)-3-hydroxypiperidine 
• 94944-61-3 (S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-2-O-(2-tetrahydropyranyl)-5-amino-1,2-pentanediol 
• 94944-66-8 (S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-5-amino-1,2-pentanediol 
• 94944-68-0 (S)-N-<(benzyloxy)carbonyl>-3-O-(2-tetrahydropyranyl)-3-piperidinol 
• 94944-64-6 (S)-N-<(benzyloxy)carbonyl>-1,2-O-isopropylidene-5-amino-1,2-pentanediol 
• 94944-65-7 (S)-N-<(benzyloxy)carbonyl>-5-amino-1,2-pentanediol 
• 158010-32-3 (R)-1-Benzyloxy-14-(tert-butyl-diphenyl-silanyloxy)-tetradecan-4-ol 
• 158110-04-4 (2S)-1,2-epoxy-5-benzyloxy-pentane 
• 172689-00-8 (2S,5S)-1,2-Bis-O-(triisopropylsilyl)-8-(pivaloyloxy)octane-1,2,5-triol 
• 172689-11-1 2,2-Dimethyl-propionic acid (4S,7S)-4-(toluene-4-sulfonyloxy)-7,8-bis-triisopropylsilanyloxy-octyl ester 
• 172689-09-7 Toluene-4-sulfonic acid (S)-1-((S)-3,4-bis-triisopropylsilanyloxy-butyl)-hexyl ester 

Relevant academic research and scientific papers

(S)-1-Boc-3-hydroxypiperidine synthesis method

The invention discloses a (S)-1-Boc-3-hydroxypiperidine synthesis method. The method utilizes (R)-glyceraldehyde acetonide as a raw material. Through witting reaction-based acetonitrile group addition, palladium-carbon-based double bond reduction, deprotection, p-tosyl selective addition, Raney nickel-based hydrogenation reduction of the nitrile group along with ring closing, and piperidine ring nitrogen Boc protection, the (S)-1-Boc-3-hydroxypiperidine is obtained. The method utilizes the cheap chiral raw material as a starting material, produces a chiral product and prevents large material consumption and a yield loss of a splitting technology.

Functionalized Diorganozinc Compounds: Key Reagents for the Synthesis of Enantiomerically Pure 2,5-Disubstituted cis- and trans-Tetrahydrofurans

1,4-Diol derivatives 4a-i were synthesized stereoselectively by either reagent- or catalyst-controlled routes using the addition of functionalized diorganozinc reagents to aldehydes.The stereoselectivities along the reagent-controlled synthetic path were in the range between 80:20 and 95:5.The stereoselectivities along the catalyst route exceeded 95:5.The 1,4-diol derivatives 4 thus obtained were transformed into enantiomerically pure cis- and trans-2,5-disubstituted tetrahydrofurans (16-20) by means of an intramolecular Williamson reaction. - Keywords: Synthesis, stereoselective / Catalysis / Tetrahydrofurans / Dialkylzinc reagents

Total synthesis of (+)-rolliniastatin 1

The first total synthesis of the naturally occurring acetogenin (+)-rolliniastatin 1 (1) has been achieved. A high degree of stereochemical control in the construction of the bis-THF system was accomplished by chelation controlled addition of functionalized organo-metallic reagents derived from 5 and 11 to α-alkoxy-aldehydes.

C-Nucleoside Studies. Part 21. Synthesis of Some Hydroxyalkylated Pyrrolo- and Thieno-pyrimidines Related to Known Antiviral Acyclonucleosides

Treatment of (S)-4,5-isopropylidenedioxypentanonitrile 17 with ethyl formate and sodium hydride gave a hydroxymethylene derivative which interacted with aminoacetonitrile to give 3-cyanomethyleneamino-2-acrylonitrile 19; this was elaborated via 3-amino-2-cyano-4-pyrrol 22 into 4-amino-7-pyrrolopyrimidine 9.Treatment of the hydroxymethylene derivative of 17 with methanesulphonyl chloride, followed by acetylthioacetonitrile and sodium carbonate in ethanol gave 3-amino-2-cyano-4-thiophene 25, convertible in two steps into 4-amino-7-thienopyrimidine 10. Similar chemistry was employed for the conversion of 5,6-isopropylidenedioxyhexanonitril 30 into the higher homologues 4-amino-7-(3,4-dihydroxybutyl)pyrrolo- and thieno-(3,2-d)pyrimidine 11 and 12, and for the preparation of 4-amino-7-(4-hydroxy-3-hydroxymethylbutyl)pyrrolopyrimidine 13 from 6-benzyloxy-5-benzyloxymethylhexanonitrile 41.The hydroxyalkylated products 9-13 are C-nucleosides analogues of known antiviral agents, but did display antiviral activity.