4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol

Base Information

• Chemical Name: 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol
• CAS No.: 161045-55-2
• Molecular Formula: C₇₂H₇₈N₄O₁₁Si
• Molecular Weight: 1203.52

Synonyms:

Chemical Property of 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol

There total 16 articles about 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol 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%

phenyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-1-thio-D-glucopyranoside (161045-54-1) + N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol (161045-53-0) → 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-β-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol + 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol (161045-55-2)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In diethyl ether; dichloromethane; at -50 ℃;

DOI:10.1246/cl.1994.2119

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) → 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol (161045-55-2)

Guidance literature:

Multi-step reaction with 14 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

With pyridine; 1H-imidazole; hydrogenchloride; N-iodo-succinimide; sodium azide; trifluorormethanesulfonic acid; 4 Angstroem MS; sodium methylate; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; triphenylphosphine; trifluoroacetic acid; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

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

Reference yield:

3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose (91882-92-7) → 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol (161045-55-2)

Guidance literature:

Multi-step reaction with 13 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

With pyridine; 1H-imidazole; hydrogenchloride; N-iodo-succinimide; sodium azide; trifluorormethanesulfonic acid; 4 Angstroem MS; sodium methylate; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; triphenylphosphine; trifluoroacetic acid; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

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

upstream raw materials:

phenyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-1-thio-D-glucopyranoside

N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol

(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

Downstream raw materials:

4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol

4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-1,5-dideoxy-1,5-imino-D-gulcitol

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

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

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