147976-19-0

Basic information

• Product Name: (4S)-2,2-dimethyl-4-[(E)-2-phenylethenyl]-1,3-dioxolane
• Synonyms: (4S)-2,2-dimethyl-4-[(E)-2-phenylethenyl]-1,3-dioxolane
• CAS NO: 147976-19-0
• Molecular Weight: 204.269
• Mol File: 147976-19-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (4S)-2,2-dimethyl-4-[(E)-2-phenylethenyl]-1,3-dioxolane(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-2,2-dimethyl-4-[(E)-2-phenylethenyl]-1,3-dioxolane(147976-19-0)
• EPA Substance Registry System: (4S)-2,2-dimethyl-4-[(E)-2-phenylethenyl]-1,3-dioxolane(147976-19-0)

Safety Data

• Hazardous Substances Data: 147976-19-0(Hazardous Substances Data)

Upstream product

• 1449-46-3 benzyltriphenylphosphonium bromide 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 100-39-0 benzyl bromide 
• 3206-48-2 BI-83B₃ 
• 1100-88-5 benzyltriphenylphosphonium chloride 

Downstream Products

• 157732-87-1 (4S)-2,2-dimethyl-4-(2-phenylethyl)-1,3-dioxolane 
• 917251-13-9 (R,2Z,6E)-5-hydroxy-7-phenylhepta-2,6-dienoate 
• 917251-12-8 (5R,2Z,6E)-5-(tert-butyldimethylsilanyloxy)-7-phenylhepta-2,6-dienoate 
• 917251-11-7 (3R,4E)-3-(tert-butyldimethylsilanyloxy)-5-phenylpent-4-enal 
• 132203-22-6 (R,E)-3-hydroxy-5-phenylpent-4-enenitrile 
• 620990-03-6 Acetic acid (1R,3R)-3-benzyloxycarbonylamino-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenyl-propyl ester 
• 620990-02-5 (4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-phenyl-[1,2,3]oxathiazinane 2,2-dioxide 
• 620990-01-4 (4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-phenyl-[1,2,3]oxathiazinane 2,2-dioxide 
• 620990-00-3 sulfamic acid 1-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenyl-propyl ester 
• 620989-99-3 1-(tert-butyl-diphenyl-silanyloxy)-4-phenyl-butan-2-ol 
• 620989-96-0 (2R,4S)-4-Amino-4-phenyl-butane-1,2-diol 
• 212560-65-1 (R)-tert-butyl (3-oxo-1-phenylpropyl)carbamate 
• 143216-63-1 (2R,4R)-4-Amino-4-phenyl-butane-1,2-diol 
• 124988-64-3 (S)-4-phenyl-1,2-butanediol 

Relevant articles and documents

The influence of α-coordinating groups of aldehydes on E/Z-selectivity and the use of quaternary ammonium counter ions for enhanced E-selectivity in the Julia–Kocienski reaction

Modified reaction conditions for improved E-selectivity of olefins in the Julia–Kocienski reaction of aldehydes having α-coordinating substituents are demonstrated. The chelating groups in aldehydes are expected to stabilize the syn-transition state with metal ions, whereas the weakly coordinating quaternary ammonium ions are devoid of all possible chelating interactions to enhance E-selectivity. A systematic investigation is presented to study the size of the neighbouring protecting groups of aldehydes and their chelation effect on E/Z-selectivity in the Julia–Kocienski reaction.

Diastereoselective Fluorocyclopropanation of Chiral Allylic Alcohols Using an α-Fluoroiodomethylzinc Carbenoid

Chiral fluorocyclopropyl carbinols were synthesized in high diastereoselectivities via a zinc mediated cyclopropanation reaction, using sec-allylic alcohols as simple building blocks. An enantioselective version of this transformation was achieved through

Synthesis of enantiomerically pure perhydrofuro[3,4-b]pyrans and perhydrofuro[3,4-b]furans

Olefinic diols, prepared from (R)-(+)-2,2-dimethyl-1,3-dioxolane-4- carboxaldehyde via olefination and hydrolysis, were converted into enantiomerically pure hydroxy substituted tetrahydrofuran derivatives by cyclization using N-phenylselenophthalimide and BF3. The PhSe group in the C-4 position of these tetrahydrofurans was then substituted by an allyl group using allyltributylstannane in the presence of AIBN. The selenium promoted cyclizations of the allyl tetrahydrofurans in which the OH and the allyl groups are trans to each other formed the enantiopure perhydrofuro[3,4-b]pyrans, while the cyclization of the allyl tetrahydrofurans in which the OH and the allyl groups are cis gave rise to the perhydrofuro[3,4-b]furans. These bicyclic products were finally deselenenylated with triphenyltin hydride and AIBN.