(3S,4S)-3-(allyloxy)-4-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]pentanenitrile

Base Information

• Chemical Name: (3S,4S)-3-(allyloxy)-4-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]pentanenitrile
• CAS No.: 866343-54-6
• Molecular Formula: C₁₉H₂₅NO₃
• Molecular Weight: 315.412
• Mol file: 866343-54-6.mol

Synonyms:(3S,4S)-3-(allyloxy)-4-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]pentanenitrile

Chemical Property of (3S,4S)-3-(allyloxy)-4-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]pentanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-(allyloxy)-4-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]pentanenitrile

There total 8 articles about (3S,4S)-3-(allyloxy)-4-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]pentanenitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(2R,3S)-2-(allyloxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butyl 4-methylbenzenesulfonate (866343-53-5) + sodium cyanide (143-33-9,25596-52-5) → (3S,4S)-3-(allyloxy)-4-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]pentanenitrile (866343-54-6)

Guidance literature:

With sodium hydrogencarbonate; In dimethyl sulfoxide; at 60 ℃; for 5h;

DOI:10.1002/chem.200500282

Reference yield:

ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate (39806-16-1) → (3S,4S)-3-(allyloxy)-4-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]pentanenitrile (866343-54-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1,4-bis-(9-O-dihydroquinidinyl)phthalazine; K₃[Fe(CN)6]; K₂OsO₄*2H₂O / K₂CO₃; CH₃SO₂NH₂ / 2-methyl-propan-2-ol / 0 °C

1.2: 8.732 g / p-TsOH*H₂O / acetone / 20 °C

2.1: 72 percent / Me₃SiCl / diethyl ether; hexane / 6 h / -78 °C

3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

3.2: oxodiperoxymolybdenum(pyridine)-hexamethylphosphorictriamide / tetrahydrofuran / 3 h / -78 °C

4.1: LDA / tetrahydrofuran / 0.33 h / -78 °C

4.2: 85 percent / tetrahydrofuran; dimethylformamide / -78 - 20 °C

5.1: 99 percent / LiAlH₄ / tetrahydrofuran / 5 - 20 °C

6.1: 94 percent / DABCO / CH₂Cl₂ / 20 °C

7.1: 99 percent / NaHCO₃ / dimethylsulfoxide / 5 h / 60 °C

With 1,4-diaza-bicyclo[2.2.2]octane; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; potassium osmate(VI); lithium aluminium tetrahydride; chloro-trimethyl-silane; sodium hydrogencarbonate; potassium hexacyanoferrate(III); lithium diisopropyl amide; methanesulfonamide; potassium carbonate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; tert-butyl alcohol;

DOI:10.1002/chem.200500282

Reference yield:

ethyl (2R,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate (866343-42-2) → (3S,4S)-3-(allyloxy)-4-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]pentanenitrile (866343-54-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran / 0.33 h / -78 °C

1.2: 85 percent / tetrahydrofuran; dimethylformamide / -78 - 20 °C

2.1: 99 percent / LiAlH₄ / tetrahydrofuran / 5 - 20 °C

3.1: 94 percent / DABCO / CH₂Cl₂ / 20 °C

4.1: 99 percent / NaHCO₃ / dimethylsulfoxide / 5 h / 60 °C

With 1,4-diaza-bicyclo[2.2.2]octane; lithium aluminium tetrahydride; sodium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1002/chem.200500282

upstream raw materials:

(2R,3S)-2-(allyloxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butyl 4-methylbenzenesulfonate

sodium cyanide

ethyl (2R,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate

(2R,3S)-2-(allyloxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butan-1-ol

Downstream raw materials:

(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

cryptophycin 52

(E)-(3S,6R,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6-methyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

cryptophycin-1