1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanone

Base Information

• Chemical Name: 1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanone
• CAS No.: 114158-32-6
• Molecular Formula: C₂₄H₃₂O₄Si
• Molecular Weight: 412.601
• Mol file: 114158-32-6.mol

Synonyms:1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanone

Chemical Property of 1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanone

There total 4 articles about 1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanone 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: 95.0%

(S)-1-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanol (105544-86-3,105616-52-2) → 1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanone (114158-32-6)

Guidance literature:

With pyridiniumchlorochromate on aluminumoxide; In dichloromethane; at 22 ℃;

DOI:10.1021/jo00244a063

Reference yield:

2,3-O-isopropylidene-L-erythrofuranose (213767-09-0) → 1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanone (114158-32-6)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / -78 °C

2: 99 percent / imidazole / dimethylformamide / -30 °C

3: 95 percent / pyridinium chlorochromate on neutral Al₂O₃ / CH₂Cl₂ / 22 °C

With 1H-imidazole; pyridiniumchlorochromate on aluminumoxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00244a063

Reference yield:

(1S)-1-[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethan-1-ol (93223-61-1,114296-87-6,117557-98-9,124990-87-0) → 1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanone (114158-32-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / imidazole / dimethylformamide / -30 °C

2: 95 percent / pyridinium chlorochromate on neutral Al₂O₃ / CH₂Cl₂ / 22 °C

With 1H-imidazole; pyridiniumchlorochromate on aluminumoxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00244a063

upstream raw materials:

(S)-1-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanol

2,3-O-isopropylidene-L-erythrofuranose

(1S)-1-[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethan-1-ol

tert-butylchlorodiphenylsilane

Downstream raw materials:

Benzoic acid (E)-4-methanesulfonyloxy-3-((1S,2S,6R,7S,8R)-7-methoxymethoxy-1,4,4-trimethyl-9-oxo-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undec-7-yl)-but-2-enyl ester

Benzoic acid 2-[(1R,2S,6R,7S,8S)-2,7-bis-methoxymethoxy-8-methyl-10-oxo-5,9-dioxa-tricyclo[6.2.1.0^2,6]undec-(3E)-ylidene]-ethyl ester

(S)-5-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-methyl-dihydro-furan-2-one

Benzoic acid 2-[(1R,2S,6R,7S,8S)-2,7-dihydroxy-8-methyl-10-oxo-5,9-dioxa-tricyclo[6.2.1.0^2,6]undec-(3E)-ylidene]-ethyl ester