benzyl 3-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate

Base Information

• Chemical Name: benzyl 3-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate
• CAS No.: 372494-13-8
• Molecular Formula: C₅₇H₆₀N₂O₁₂
• Molecular Weight: 965.11

Synonyms:benzyl 3-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate

Chemical Property of benzyl 3-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of benzyl 3-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate

There total 27 articles about benzyl 3-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate 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: 77.0%

benzyl 3-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate (161045-57-4) → benzyl 3-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate (372494-13-8)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(01)00642-1

Reference yield:

(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole (20316-77-2) → benzyl 3-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate (372494-13-8)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 175 g / acetic acid; H₂O / 16 h / 60 °C

2.1: CH₂Cl₂; pyridine / 1 h / -15 °C

3.1: 179 g / CH₂Cl₂; pyridine / 20 h / -15 - 20 °C

4.1: NaOMe / methanol; tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

4.2: 78 percent / t-BuOK / dimethylformamide; tetrahydrofuran / 6 h / 0 - 20 °C

5.1: 3.70 g / NH₄Cl; NaN₃ / dimethylformamide; H₂O / 2 h / 80 °C

6.1: 3.84 g / n-tetrabutylammonium iodide; NaH / dimethylformamide / 2.5 h / 0 °C

7.1: 50 percent / 3 percent HCl / 18 h / 20 °C

8.1: 44.1 g / pyridine / CH₂Cl₂ / 1.6 h / -60 °C

9.1: PPh₃ / CH₂Cl₂ / 4 h / 20 - 45 °C

9.2: K₂CO₃ / H₂O; tetrahydrofuran; methanol / 96 h / 20 °C

9.3: 27.3 g / tetrahydrofuran; methanol; H₂O / 7 h / 0 °C

10.1: TFA / dioxane; H₂O / 11 h / 20 °C

10.2: 71 percent / NaBH₄ / ethanol / 2 h / 0 °C

11.1: imidazole / dimethylformamide / 1 h / 20 °C

12.1: 3.76 g / tetrabutylammonium iodide; NaH / dimethylformamide / 3 h / 0 °C

13.1: 72 percent / sodium acetate / PdCl₂ / acetic acid; H₂O / 3.5 h / 50 °C

14.1: 77 percent / 4 Angstroem MS; NIS; TfOH / diethyl ether; CH₂Cl₂ / 0.83 h / -50 °C

15.1: PPh₃ / tetrahydrofuran / 16 h / 60 °C

15.2: 93 percent / H₂O / 3 h / 20 °C

16.1: 99 percent / AcOH; TBAF / tetrahydrofuran / 22 h / 20 °C

17.1: Jones reagent / acetone / 0.17 h / 20 °C

18.1: 43 mg / cesium carbonate / dimethylformamide / 6 h / 20 °C

19.1: 77 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; N-iodo-succinimide; sodium azide; jones reagent; trifluorormethanesulfonic acid; 4 Angstroem MS; tetrabutyl ammonium fluoride; sodium methylate; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; caesium carbonate; acetic acid; triphenylphosphine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)00642-1

Reference yield:

3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose (91882-92-7) → benzyl 3-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate (372494-13-8)

Guidance literature:

Multi-step reaction with 18 steps

1.1: CH₂Cl₂; pyridine / 1 h / -15 °C

2.1: 179 g / CH₂Cl₂; pyridine / 20 h / -15 - 20 °C

3.1: NaOMe / methanol; tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

3.2: 78 percent / t-BuOK / dimethylformamide; tetrahydrofuran / 6 h / 0 - 20 °C

4.1: 3.70 g / NH₄Cl; NaN₃ / dimethylformamide; H₂O / 2 h / 80 °C

5.1: 3.84 g / n-tetrabutylammonium iodide; NaH / dimethylformamide / 2.5 h / 0 °C

6.1: 50 percent / 3 percent HCl / 18 h / 20 °C

7.1: 44.1 g / pyridine / CH₂Cl₂ / 1.6 h / -60 °C

8.1: PPh₃ / CH₂Cl₂ / 4 h / 20 - 45 °C

8.2: K₂CO₃ / H₂O; tetrahydrofuran; methanol / 96 h / 20 °C

8.3: 27.3 g / tetrahydrofuran; methanol; H₂O / 7 h / 0 °C

9.1: TFA / dioxane; H₂O / 11 h / 20 °C

9.2: 71 percent / NaBH₄ / ethanol / 2 h / 0 °C

10.1: imidazole / dimethylformamide / 1 h / 20 °C

11.1: 3.76 g / tetrabutylammonium iodide; NaH / dimethylformamide / 3 h / 0 °C

12.1: 72 percent / sodium acetate / PdCl₂ / acetic acid; H₂O / 3.5 h / 50 °C

13.1: 77 percent / 4 Angstroem MS; NIS; TfOH / diethyl ether; CH₂Cl₂ / 0.83 h / -50 °C

14.1: PPh₃ / tetrahydrofuran / 16 h / 60 °C

14.2: 93 percent / H₂O / 3 h / 20 °C

15.1: 99 percent / AcOH; TBAF / tetrahydrofuran / 22 h / 20 °C

16.1: Jones reagent / acetone / 0.17 h / 20 °C

17.1: 43 mg / cesium carbonate / dimethylformamide / 6 h / 20 °C

18.1: 77 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; N-iodo-succinimide; sodium azide; jones reagent; trifluorormethanesulfonic acid; 4 Angstroem MS; tetrabutyl ammonium fluoride; sodium methylate; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; caesium carbonate; acetic acid; triphenylphosphine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)00642-1

upstream raw materials:

benzyl 3-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate

(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose

benzyl chloroformate

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