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

Base Information

• Chemical Name: Benzyl 5-O-(aminocarbonyl)-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate
• CAS No.: 205449-15-6
• Molecular Formula: C₂₁H₃₀N₂O₈
• Molecular Weight: 438.478
• Mol file: 205449-15-6.mol

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

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

There total 15 articles about Benzyl 5-O-(aminocarbonyl)-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: 82.0%

methyl 5-O-(aminocarbonyl)-2-<(N-tert-butoxycarbonyl)amino>-2-deoxy-3,4-O-isopropylidene-L-xylonate (105309-43-1) + benzyl alcohol (100-51-6,185532-71-2) → Benzyl 5-O-(aminocarbonyl)-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate (205449-15-6)

Guidance literature:

With titanium(IV) isopropylate; In benzene; Heating;

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) → Benzyl 5-O-(aminocarbonyl)-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate (205449-15-6)

Guidance literature:

Multi-step reaction with 12 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

9: 94 percent / HF; H₂O; pyridine / 3 h / 20 °C

10: Et₃N; pyridine / tetrahydrofuran; diethyl ether / 1 h / -20 °C

11: NH₃ / methanol / 0.5 h / 0 °C

12: 82 percent / Ti(O-i-Pr)4 / benzene / 12 h / Heating

With pyridine; titanium(IV) isopropylate; sodium azide; hydrogen fluoride; ammonia; water; hydrogen; potassium carbonate; triethylamine; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Deacetylation / 2: Esterification / 3: Substitution / 4: Deacetylation / 5: Esterification / 6: Substitution / 7: Catalytic hydrogenation / 8: Acylation / 9: desilylation / 10: Carbonylation / 11: Substitution / 12: 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 → Benzyl 5-O-(aminocarbonyl)-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate (205449-15-6)

Guidance literature:

Multi-step reaction with 10 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

7: 94 percent / HF; H₂O; pyridine / 3 h / 20 °C

8: Et₃N; pyridine / tetrahydrofuran; diethyl ether / 1 h / -20 °C

9: NH₃ / methanol / 0.5 h / 0 °C

10: 82 percent / Ti(O-i-Pr)4 / benzene / 12 h / Heating

With pyridine; titanium(IV) isopropylate; sodium azide; hydrogen fluoride; ammonia; water; hydrogen; potassium carbonate; triethylamine; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Esterification / 2: Deacetylation / 3: Esterification / 4: Substitution / 5: Catalytic hydrogenation / 6: Acylation / 7: desilylation / 8: Carbonylation / 9: Substitution / 10: Substitution;

DOI:10.1055/s-1999-3563

upstream raw materials:

methyl 5-O-(aminocarbonyl)-2-<(N-tert-butoxycarbonyl)amino>-2-deoxy-3,4-O-isopropylidene-L-xylonate

benzyl alcohol

methyl 2-N-[(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

Downstream raw materials:

Polyoxin L

Polyoxin D

5-((2-amino-5-O-(carbamoyl)-2-deoxy-L-xylon)amido)-1,5-dideoxy-1-(3,4-dihydro-5-(hydroxymethyl)-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-allofuranuronic acid