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

Base Information

• Chemical Name: Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid methyl ester
• CAS No.: 205449-09-8
• Molecular Formula: C₂₇H₃₆O₇Si
• Molecular Weight: 500.664
• Mol file: 205449-09-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid → Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid methyl ester (205449-09-8)

Guidance literature:

Yield given;

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

Reference yield: 54.0%

Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid methyl ester (205449-09-8) → Methyl 5-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-L-xylonate (205449-10-1) + Methyl 5-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-L-lyxonate (205449-07-6)

Guidance literature:

With methanol; potassium carbonate;

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) → Methyl 5-O-tert-butyldiphenylsilyl-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate (205449-13-4)

Guidance literature:

Multi-step reaction with 8 steps

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

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

3: dimethylformamide / 1 h

4: 87 percent / K₂CO₃ / methanol / 1 h / 0 °C

5: pyridine / CH₂Cl₂ / 0.33 h / 0 °C

6: NaN₃ / dimethylformamide / 0.5 h / 20 °C

7: H₂ / 20 percent Pd(OH)2/C / methanol / 12 h / 20 °C

8: Et₃N / dioxane / 1.25 h / 20 °C

With pyridine; sodium azide; hydrogen; potassium carbonate; triethylamine; palladium dihydroxide; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Deacetylation / 2: Esterification / 3: Substitution / 4: Deacetylation / 5: Esterification / 6: Substitution / 7: Catalytic hydrogenation / 8: Acylation;

DOI:10.1055/s-1999-3563

upstream raw materials:

diazomethane

Downstream raw materials:

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

Methyl 5-O-tert-butyldiphenylsilyl-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