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

Base Information

Chemical Name:2,5-diamino-3,4-di-O-benzyl-2-N-acetamido-2,5-dideoxy-D-xylo-1,5-thionolactam
CAS No.:262380-51-8
Molecular Formula:C₂₁H₂₄N₂O₃S
Molecular Weight:384.499
Hs Code.:

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

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

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

There total 14 articles about 2,5-diamino-3,4-di-O-benzyl-2-N-acetamido-2,5-dideoxy-D-xylo-1,5-thionolactam 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: 43.0%

: 108-24-7
acetic anhydride

: 262380-50-7
2,5-diamino-3,4-di-O-benzyl-2-N-tert-butyloxycarbonyl-2,5-dideoxy-D-xylothiono-1,5-lactam

: 262380-51-8
2,5-diamino-3,4-di-O-benzyl-2-N-acetamido-2,5-dideoxy-D-xylo-1,5-thionolactam

Guidance literature:: 2,5-diamino-3,4-di-O-benzyl-2-N-tert-butyloxycarbonyl-2,5-dideoxy-D-xylothiono-1,5-lactam; With 2,6-dimethylpyridine; t-butyldimethylsiyl triflate; In dichloromethane; at 20 ℃; for 2h;

acetic anhydride; With tetrabutyl ammonium fluoride; In methanol; dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/S0008-6215(03)00239-8

Reference yield:

: 123751-18-8
(E)-3-<(4R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl>-2-propen-1-ol

: 262380-51-8
2,5-diamino-3,4-di-O-benzyl-2-N-acetamido-2,5-dideoxy-D-xylo-1,5-thionolactam

Guidance literature:: Multi-step reaction with 10 steps

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

2.1: 2.45 g / sodium azide / dimethylformamide / 1.5 h / 20 °C

3.1: 39 percent / morpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 24 h / 20 °C

4.1: 94 percent / NaH / dimethylformamide / 3 h / 0 °C

5.1: 75 percent / DOWEX 50W H⁽¹⁺⁾ resin / methanol / 48 h / 20 °C

6.1: 2,2,6,6-tetramethyl-1-pyperidinyloxy radical; potassium bromide; sodium hypochlorite / acetone; aq. NaHCO₃ / 0.67 h / 0 °C

7.1: methanol; diethyl ether

8.1: 85 percent / hydrogen / Pd/CaCO₃ / methanol / 12 h

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

10.1: TBDMSOTf; 2,6-lutidine / CH₂Cl₂ / 2 h / 20 °C

10.2: 43 percent / tetrabutylammonium fluoride / CH₂Cl₂; methanol / 1 h / 20 °C

With Lawessons reagent; 2,6-dimethylpyridine; 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; t-butyldimethylsiyl triflate; 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:

: 131713-27-4,134525-18-1,144070-31-5,149406-02-0
(4R)-4-(2-ethoxycarbonyl-vinyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 262380-51-8
2,5-diamino-3,4-di-O-benzyl-2-N-acetamido-2,5-dideoxy-D-xylo-1,5-thionolactam

Guidance literature:: Multi-step reaction with 11 steps

1.1: 93 percent / DIBAL-H / tetrahydrofuran / 1.5 h / 0 °C

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

3.1: 2.45 g / sodium azide / dimethylformamide / 1.5 h / 20 °C

4.1: 39 percent / morpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 24 h / 20 °C

5.1: 94 percent / NaH / dimethylformamide / 3 h / 0 °C

6.1: 75 percent / DOWEX 50W H⁽¹⁺⁾ resin / methanol / 48 h / 20 °C

7.1: 2,2,6,6-tetramethyl-1-pyperidinyloxy radical; potassium bromide; sodium hypochlorite / acetone; aq. NaHCO₃ / 0.67 h / 0 °C

8.1: methanol; diethyl ether

9.1: 85 percent / hydrogen / Pd/CaCO₃ / methanol / 12 h

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

11.1: TBDMSOTf; 2,6-lutidine / CH₂Cl₂ / 2 h / 20 °C

11.2: 43 percent / tetrabutylammonium fluoride / CH₂Cl₂; methanol / 1 h / 20 °C

With Lawessons reagent; 2,6-dimethylpyridine; 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; t-butyldimethylsiyl triflate; 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