N-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl]-2-tert-butoxycarbonylamino-succinamic acid allyl ester

Base Information

• Chemical Name: N-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl]-2-tert-butoxycarbonylamino-succinamic acid allyl ester
• CAS No.: 344597-17-7
• Molecular Formula: C₅₆H₆₈N₄O₁₅
• Molecular Weight: 1037.17
• Mol file: 344597-17-7.mol

Synonyms:

Chemical Property of N-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl]-2-tert-butoxycarbonylamino-succinamic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl]-2-tert-butoxycarbonylamino-succinamic acid allyl ester

There total 12 articles about N-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl]-2-tert-butoxycarbonylamino-succinamic acid allyl ester 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:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → N-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl]-2-tert-butoxycarbonylamino-succinamic acid allyl ester (344597-17-7)

Guidance literature:

Multi-step reaction with 12 steps

1: NH₂NH₂; AcOH / dimethylformamide

2: imidazole; 4-dimethylaminopyridine / dimethylformamide

3: t-BuOK / methanol; tetrahydrofuran

4: camphorsulfonic acid / acetonitrile

5: NaH / dimethylformamide

6: tetrabutylammonium fluoride; AcOH / tetrahydrofuran

7: dimethylaminosulfur trifluoride / tetrahydrofuran

8: 81 percent / Cp₂HfCl₂; AgClO₄ / CH₂Cl₂

9: ethylenediamine / butan-1-ol

10: methanol

11: H₂ / Pd/C(ethylenediamine poisoned) / CH₂Cl₂; methanol

12: 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide / CH₂Cl₂

With 1H-imidazole; dmap; bis(cyclopentadienyl)hafnium dichloride; dimethylaminosulphur trifluoride; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; silver perchlorate; sodium hydride; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; ethylenediamine; hydrazine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; butan-1-ol;

DOI:10.1016/S0040-4039(01)00342-2

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (72858-55-0) → N-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl]-2-tert-butoxycarbonylamino-succinamic acid allyl ester (344597-17-7)

Guidance literature:

Multi-step reaction with 11 steps

1: imidazole; 4-dimethylaminopyridine / dimethylformamide

2: t-BuOK / methanol; tetrahydrofuran

3: camphorsulfonic acid / acetonitrile

4: NaH / dimethylformamide

5: tetrabutylammonium fluoride; AcOH / tetrahydrofuran

6: dimethylaminosulfur trifluoride / tetrahydrofuran

7: 81 percent / Cp₂HfCl₂; AgClO₄ / CH₂Cl₂

8: ethylenediamine / butan-1-ol

9: methanol

10: H₂ / Pd/C(ethylenediamine poisoned) / CH₂Cl₂; methanol

11: 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide / CH₂Cl₂

With 1H-imidazole; dmap; bis(cyclopentadienyl)hafnium dichloride; dimethylaminosulphur trifluoride; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; silver perchlorate; sodium hydride; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; ethylenediamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; butan-1-ol;

DOI:10.1016/S0040-4039(01)00342-2

Reference yield:

3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (277310-81-3) → N-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl]-2-tert-butoxycarbonylamino-succinamic acid allyl ester (344597-17-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / Cp₂HfCl₂; AgClO₄ / CH₂Cl₂

2: ethylenediamine / butan-1-ol

3: methanol

4: H₂ / Pd/C(ethylenediamine poisoned) / CH₂Cl₂; methanol

5: 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide / CH₂Cl₂

With bis(cyclopentadienyl)hafnium dichloride; hydrogen; silver perchlorate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; ethylenediamine; palladium on activated charcoal; In methanol; dichloromethane; butan-1-ol;

DOI:10.1016/S0040-4039(01)00342-2

upstream raw materials:

N-tert-Butoxycarbonyl-L-asaraginsaeure-α-allylester

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride