(S)-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-trifluoromethanesulfonyloxy-acetic acid methyl ester

Base Information

• Chemical Name: (S)-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-trifluoromethanesulfonyloxy-acetic acid methyl ester
• CAS No.: 205449-11-2
• Molecular Formula: C₂₆H₃₃F₃O₈SSi
• Molecular Weight: 590.69
• Mol file: 205449-11-2.mol

Synonyms:(S)-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-trifluoromethanesulfonyloxy-acetic acid methyl ester

Chemical Property of (S)-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-trifluoromethanesulfonyloxy-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-trifluoromethanesulfonyloxy-acetic acid methyl ester

There total 3 articles about (S)-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-trifluoromethanesulfonyloxy-acetic acid methyl ester 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: 90.0%

trifluoromethylsulfonic anhydride (358-23-6) + Methyl 5-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-L-xylonate (205449-10-1) → (S)-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-trifluoromethanesulfonyloxy-acetic acid methyl ester (205449-11-2)

Guidance literature:

With pyridine; In dichloromethane;

DOI:10.3987/COM-97-S(N)59

Reference yield:

Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid methyl ester (205449-09-8) → (S)-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-trifluoromethanesulfonyloxy-acetic acid methyl ester (205449-11-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / K₂CO₃ / methanol / 0.67 h / 0 °C

2: 90 percent / pyridine / CH₂Cl₂ / 0.33 h / 0 °C

With pyridine; potassium carbonate; In methanol; dichloromethane; 1: Deacetylation / 2: Esterification;

DOI:10.1055/s-1999-3563

Reference yield:

Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid → (S)-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-trifluoromethanesulfonyloxy-acetic acid methyl ester (205449-11-2)

Guidance literature:

Multi-step reaction with 3 steps

2: 45 percent / K₂CO₃, MeOH

3: 90 percent / pyridine / CH₂Cl₂

With pyridine; methanol; potassium carbonate; In dichloromethane;

DOI:10.3987/COM-97-S(N)59

upstream raw materials:

trifluoromethylsulfonic anhydride

Methyl 5-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-L-xylonate

Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid methyl ester

Downstream raw materials:

(R)-Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid methyl ester

Methyl 2-azido-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-isopropylidene-L-lyxonate

Benzyl 5-O-(aminocarbonyl)-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate

Methyl 2-azido-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-isopropylidene-L-xylonate