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

Base Information

• Chemical Name: 2,5-diamino-3,4-di-O-benzyl-2-N-tert-butyloxycarbonyl-2,5-dideoxy-D-xylothiono-1,5-lactam
• CAS No.: 262380-50-7
• Molecular Formula: C₂₄H₃₀N₂O₄S
• Molecular Weight: 442.579
• Mol file: 262380-50-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about 2,5-diamino-3,4-di-O-benzyl-2-N-tert-butyloxycarbonyl-2,5-dideoxy-D-xylothiono-1,5-lactam 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%

2,5-diamino-3,4-di-O-benzyl-2-N-tert-butyloxycarbonyl-2,5-dideoxy-D-xylono-1,5-lactam (262380-49-4) → 2,5-diamino-3,4-di-O-benzyl-2-N-tert-butyloxycarbonyl-2,5-dideoxy-D-xylothiono-1,5-lactam (262380-50-7)

Guidance literature:

With Lawessons reagent; pyridine; In toluene; for 2h; Heating;

DOI:10.1016/S0040-4039(99)01964-4

Reference yield:

(E)-3-<(4R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl>-2-propen-1-ol (123751-18-8) → 2,5-diamino-3,4-di-O-benzyl-2-N-tert-butyloxycarbonyl-2,5-dideoxy-D-xylothiono-1,5-lactam (262380-50-7)

Guidance literature:

Multi-step reaction with 9 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

6: 2,2,6,6-tetramethyl-1-pyperidinyloxy radical; potassium bromide; sodium hypochlorite / acetone; aq. NaHCO₃ / 0.67 h / 0 °C

7: methanol; diethyl ether

8: 85 percent / hydrogen / Pd/CaCO₃ / methanol / 12 h

9: Lawesson's reagent / tetrahydrofuran / 1 h / 20 °C

With Lawessons reagent; 4-morpholinyl-N-oxide; sodium hypochlorite; osmium(VIII) oxide; sodium azide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; DOWEX 50W H⁽¹⁺⁾ resin; hydrogen; sodium hydride; triethylamine; potassium bromide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; sodium hydrogencarbonate; N,N-dimethyl-formamide; acetone; 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) → 2,5-diamino-3,4-di-O-benzyl-2-N-tert-butyloxycarbonyl-2,5-dideoxy-D-xylothiono-1,5-lactam (262380-50-7)

Guidance literature:

Multi-step reaction with 10 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

7: 2,2,6,6-tetramethyl-1-pyperidinyloxy radical; potassium bromide; sodium hypochlorite / acetone; aq. NaHCO₃ / 0.67 h / 0 °C

8: methanol; diethyl ether

9: 85 percent / hydrogen / Pd/CaCO₃ / methanol / 12 h

10: Lawesson's reagent / tetrahydrofuran / 1 h / 20 °C

With Lawessons reagent; 4-morpholinyl-N-oxide; sodium hypochlorite; osmium(VIII) oxide; sodium azide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; DOWEX 50W H⁽¹⁺⁾ resin; hydrogen; sodium hydride; diisobutylaluminium hydride; triethylamine; potassium bromide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; sodium hydrogencarbonate; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

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

upstream raw materials:

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

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

benzyl bromide

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

Downstream raw materials:

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