(3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-one

Base Information

• Chemical Name: (3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-one
• CAS No.: 444105-66-2
• Molecular Formula: C₁₃H₂₆O₃Si
• Molecular Weight: 258.433
• Mol file: 444105-66-2.mol

Synonyms:(3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-one

Chemical Property of (3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-one

There total 1 articles about (3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-one 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: 100.0%

(R)-3-[(2R,3S,4S)-3-[(tert-butyldimethylsilanyl)oxy]-5-hydroxy-2,4-dimethylpentanoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one (443761-68-0) → (R)-4-(1-methylethyl)-5,5-diphenyl-1,3-oxazolidin-2-one (191090-32-1) + (3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-one (444105-66-2)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/op049950l

Reference yield:

(3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-one (444105-66-2) → (2S,3S,4R,8R,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundec-6-en-5-one (845780-33-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C

1.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

1.3: LDA / tetrahydrofuran; hexane; heptane / 0.5 h / -78 °C

2.1: 818 mg / tetrahydrofuran; hexane; heptane / -78 - 20 °C

3.1: 83 mg / Ba(OH)2*8H₂O / tetrahydrofuran; H₂O / 6 h / 20 °C

With barium dihydroxide; n-butyllithium; In tetrahydrofuran; hexane; n-heptane; water; 3.1: Horner-Wadsworth-Emmons coupling;

DOI:10.1021/ol0478279

Reference yield:

(3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-one (444105-66-2) → (2S,3S,4R,8S,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundecan-5-one (845780-44-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C

1.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

1.3: LDA / tetrahydrofuran; hexane; heptane / 0.5 h / -78 °C

2.1: 818 mg / tetrahydrofuran; hexane; heptane / -78 - 20 °C

3.1: 83 mg / Ba(OH)2*8H₂O / tetrahydrofuran; H₂O / 6 h / 20 °C

4.1: 88 percent / NiCl₂*6H₂O; NaBH₄ / methanol / 0.75 h / 0 °C

With barium dihydroxide; sodium tetrahydroborate; n-butyllithium; nickel dichloride; In tetrahydrofuran; methanol; hexane; n-heptane; water; 3.1: Horner-Wadsworth-Emmons coupling;

DOI:10.1021/ol0478279

upstream raw materials:

(R)-3-[(2R,3S,4S)-3-[(tert-butyldimethylsilanyl)oxy]-5-hydroxy-2,4-dimethylpentanoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one

Downstream raw materials:

(2R,3R,4S,5S,6S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanal

(2S,4S,5S)-4-[(1S,2S,3S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

(3R,4R,5S,6S,7S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5,7-trimethyl-octan-2-one

(2S,3S,6R,7R,8S,9S,10S)-1,9,11-Tris-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-7-(4-methoxy-benzyloxy)-2,6,8,10-tetramethyl-undecan-5-one