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

Base Information

• Chemical Name: 4-amino-1-azido-2,3-di-O-benzyl-4-(N-tert-butyloxycarbonyl)-1,4-dideoxy-4,5-N,O-isopropylidene-L-arabinitol
• CAS No.: 605658-04-6
• Molecular Formula: C₂₇H₃₆N₄O₅
• Molecular Weight: 496.607
• Mol file: 605658-04-6.mol

Synonyms:4-amino-1-azido-2,3-di-O-benzyl-4-(N-tert-butyloxycarbonyl)-1,4-dideoxy-4,5-N,O-isopropylidene-L-arabinitol

Chemical Property of 4-amino-1-azido-2,3-di-O-benzyl-4-(N-tert-butyloxycarbonyl)-1,4-dideoxy-4,5-N,O-isopropylidene-L-arabinitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-amino-1-azido-2,3-di-O-benzyl-4-(N-tert-butyloxycarbonyl)-1,4-dideoxy-4,5-N,O-isopropylidene-L-arabinitol

There total 4 articles about 4-amino-1-azido-2,3-di-O-benzyl-4-(N-tert-butyloxycarbonyl)-1,4-dideoxy-4,5-N,O-isopropylidene-L-arabinitol 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: 94.0%

benzyl bromide (100-39-0) + 4-amino-1-azido-4-(N-tert-butyloxycarbonyl)-1,4-dideoxy-4,5-N,O-isopropylidene-L-arabinitol (262380-44-9) → 4-amino-1-azido-2,3-di-O-benzyl-4-(N-tert-butyloxycarbonyl)-1,4-dideoxy-4,5-N,O-isopropylidene-L-arabinitol (605658-04-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 3h;

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) → 4-amino-1-azido-2,3-di-O-benzyl-4-(N-tert-butyloxycarbonyl)-1,4-dideoxy-4,5-N,O-isopropylidene-L-arabinitol (605658-04-6)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 31 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

With 4-morpholinyl-N-oxide; osmium(VIII) oxide; sodium azide; sodium hydride; triethylamine; In tetrahydrofuran; 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) → 4-amino-1-azido-2,3-di-O-benzyl-4-(N-tert-butyloxycarbonyl)-1,4-dideoxy-4,5-N,O-isopropylidene-L-arabinitol (605658-04-6)

Guidance literature:

Multi-step reaction with 5 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: 31 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

With 4-morpholinyl-N-oxide; osmium(VIII) oxide; sodium azide; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

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

upstream raw materials:

benzyl bromide

4-amino-1-azido-4-(N-tert-butyloxycarbonyl)-1,4-dideoxy-4,5-N,O-isopropylidene-L-arabinitol

(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

Downstream raw materials:

4-amino-1-azido-2,3-di-O-benzyl-4-(N-tert-butyloxycarbonyl)-1,4-dideoxy-L-methylarabinonate

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

4-amino-1-azido-2,3-di-O-benzyl-4-(N-tert-butyloxycarbonyl)-1,4-dideoxy-L-arabinitol