(-)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-one

Base Information

• Chemical Name: (-)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-one
• CAS No.: 681853-95-2
• Molecular Formula: C₂₅H₃₂O₄Si
• Molecular Weight: 424.612
• Mol file: 681853-95-2.mol

Synonyms:(-)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-one

Chemical Property of (-)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-one

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-one

There total 9 articles about (-)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-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: 99.0%

(1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol (681853-93-0) → (-)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-one (681853-95-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/j.tet.2007.06.100

Reference yield: 97.0%

C25H34O4Si → (-)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-one (681853-95-2)

Guidance literature:

With sulfur trioxide pyridine complex; triethylamine; In dichloromethane;

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → (-)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-one (681853-95-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / triethylamine; DMAP / CH₂Cl₂ / 3 h / 20 °C

2.1: potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C

2.2: 86 percent / tetrahydrofuran / 7 h / 0 - 20 °C

3.1: 99 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

With dmap; oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 2.2: Wittig reaction / 3.1: Swern oxidation;

DOI:10.1016/j.tet.2007.06.100

upstream raw materials:

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

2,3-O-isopropylidene-D-ribofuranose

D-ribose

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

Downstream raw materials:

(3aR,4R,6aR)-(6-benzyloxymethyl-5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yloxy)-tert-butyl-diphenyl-silane

RX-3117

(3R,4S,5S)-3-(benzyloxymethyl)-1,6-dien-4,5-(O-isopropylidenedioxy)-heptan-3-ol

((3aR,4R,6aR)-6-(benzyloxymethyl)-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)(tert-butyl)diphenylsilane