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

Base Information

• Chemical Name: Methyl 2-azido-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-isopropylidene-L-xylonate
• CAS No.: 205449-12-3
• Molecular Formula: C₂₅H₃₃N₃O₅Si
• Molecular Weight: 483.64
• Mol file: 205449-12-3.mol

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

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

There total 9 articles about Methyl 2-azido-5-O-tert-butyldiphenylsilyl-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:

(R)-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-trifluoromethanesulfonyloxy-acetic acid methyl ester → Methyl 2-azido-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-isopropylidene-L-xylonate (205449-12-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; Yield given;

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

Guidance literature:

Multi-step reaction with 6 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

With pyridine; sodium azide; potassium carbonate; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Deacetylation / 2: Esterification / 3: Substitution / 4: Deacetylation / 5: Esterification / 6: Substitution;

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

Guidance literature:

Multi-step reaction with 4 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

With pyridine; sodium azide; potassium carbonate; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Deacetylation / 3: Esterification / 4: Substitution;

DOI:10.1055/s-1999-3563

upstream raw materials:

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

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

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

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

Downstream raw materials:

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

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

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