2-amino-5-azido-3,4-di-O-benzyl-2-(N-tert-butyloxycarbonyl)-2,5-dideoxy-D-xylitol

Base Information

• Chemical Name: 2-amino-5-azido-3,4-di-O-benzyl-2-(N-tert-butyloxycarbonyl)-2,5-dideoxy-D-xylitol
• CAS No.: 262380-47-2
• Molecular Formula: C₂₄H₃₂N₄O₅
• Molecular Weight: 456.542
• Mol file: 262380-47-2.mol

Synonyms:2-amino-5-azido-3,4-di-O-benzyl-2-(N-tert-butyloxycarbonyl)-2,5-dideoxy-D-xylitol

Chemical Property of 2-amino-5-azido-3,4-di-O-benzyl-2-(N-tert-butyloxycarbonyl)-2,5-dideoxy-D-xylitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-amino-5-azido-3,4-di-O-benzyl-2-(N-tert-butyloxycarbonyl)-2,5-dideoxy-D-xylitol

There total 7 articles about 2-amino-5-azido-3,4-di-O-benzyl-2-(N-tert-butyloxycarbonyl)-2,5-dideoxy-D-xylitol 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: 75.0%

2-amino-5-azido-3,4-di-O-benzyl-2-(N-tert-butyloxycarbonyl)-2,5-dideoxy-1,2-N,O-isopropylidene-D-xylitol (262380-46-1) → 2-amino-5-azido-3,4-di-O-benzyl-2-(N-tert-butyloxycarbonyl)-2,5-dideoxy-D-xylitol (262380-47-2)

Guidance literature:

With DOWEX 50W H⁽¹⁺⁾ resin; In methanol; at 20 ℃; for 48h;

DOI:10.1016/S0008-6215(03)00239-8

Reference yield:

(E)-3-<(4R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl>-2-propen-1-ol (123751-18-8) → 2-amino-5-azido-3,4-di-O-benzyl-2-(N-tert-butyloxycarbonyl)-2,5-dideoxy-D-xylitol (262380-47-2)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

2: 2.45 g / sodium azide / dimethylformamide / 1.5 h / 20 °C

3: 39 percent / morpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 24 h / 20 °C

4: 94 percent / NaH / dimethylformamide / 3 h / 0 °C

5: 75 percent / DOWEX 50W H⁽¹⁺⁾ resin / methanol / 48 h / 20 °C

With 4-morpholinyl-N-oxide; osmium(VIII) oxide; sodium azide; DOWEX 50W H⁽¹⁺⁾ resin; sodium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/S0008-6215(03)00239-8

Reference yield:

(4R)-4-(2-ethoxycarbonyl-vinyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (131713-27-4,134525-18-1,144070-31-5,149406-02-0) → 2-amino-5-azido-3,4-di-O-benzyl-2-(N-tert-butyloxycarbonyl)-2,5-dideoxy-D-xylitol (262380-47-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / DIBAL-H / tetrahydrofuran / 1.5 h / 0 °C

2: triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

3: 2.45 g / sodium azide / dimethylformamide / 1.5 h / 20 °C

4: 39 percent / morpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 24 h / 20 °C

5: 94 percent / NaH / dimethylformamide / 3 h / 0 °C

6: 75 percent / DOWEX 50W H⁽¹⁺⁾ resin / methanol / 48 h / 20 °C

With 4-morpholinyl-N-oxide; osmium(VIII) oxide; sodium azide; DOWEX 50W H⁽¹⁺⁾ resin; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/S0008-6215(03)00239-8

upstream raw materials:

2-amino-5-azido-3,4-di-O-benzyl-2-(N-tert-butyloxycarbonyl)-2,5-dideoxy-1,2-N,O-isopropylidene-D-xylitol

(E)-3-<(4R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl>-2-propen-1-ol

(4R)-4-(2-ethoxycarbonyl-vinyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

1-azido-3-(N-tert-butyloxycarbonyl-2,2-dimethyloxazolidin-4-yl)-2-propen

Downstream raw materials:

2,5-diamino-3,4-di-O-benzyl-2-N-acetamido-2,5-dideoxy-D-xylo-1,5-thionolactam

2,5-diamino-3,4-di-O-benzyl-2-N-tert-butyloxycarbonyl-2,5-dideoxy-D-xylono-1,5-lactam

2,5-diamino-3,4-di-O-benzyl-2-N-tert-butyloxycarbonyl-2,5-dideoxy-D-xylothiono-1,5-lactam

2-amino-5-azido-3,4-di-O-benzyl-2-(N-tert-butyloxycarbonyl)-2,5-dideoxy-D-methylxylonate