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

Base Information

• Chemical Name: Methyl 5-O-tert-butyldiphenylsilyl-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate
• CAS No.: 205449-13-4
• Molecular Formula: C₃₀H₄₃NO₇Si
• Molecular Weight: 557.759
• Mol file: 205449-13-4.mol

Synonyms:Methyl 5-O-tert-butyldiphenylsilyl-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate

Chemical Property of Methyl 5-O-tert-butyldiphenylsilyl-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 5-O-tert-butyldiphenylsilyl-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate

There total 19 articles about Methyl 5-O-tert-butyldiphenylsilyl-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate 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:

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

Reference yield:

Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid → 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 6 steps

1: diethyl ether / 0.5 h / 20 °C

2: 87 percent / K₂CO₃ / methanol / 1 h / 0 °C

3: pyridine / CH₂Cl₂ / 0.33 h / 0 °C

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

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

6: Et₃N / dioxane / 1.25 h / 20 °C

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

DOI:10.1055/s-1999-3563

Reference yield:

Methyl 2-azido-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-isopropylidene-L-xylonate (205449-12-3) → 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 2 steps

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

2: Et₃N / dioxane / 1.25 h / 20 °C

With hydrogen; triethylamine; palladium dihydroxide; In 1,4-dioxane; methanol; 1: Catalytic hydrogenation / 2: Acylation;

DOI:10.1055/s-1999-3563

upstream raw materials:

di-tert-butyl dicarbonate

(E)-5-Benzyloxy-1-((R)-toluene-4-sulfinyl)-pent-3-en-2-one

5-benzyloxy-1-(S_R)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol

5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol

Downstream raw materials:

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

Polyoxin L