p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside

Base Information

• Chemical Name: p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside
• CAS No.: 359687-25-5
• Molecular Formula: C₃₈H₅₀N₂O₁₀
• Molecular Weight: 694.822

Synonyms:p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside

Chemical Property of p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside

Chemical Property:

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Technology Process of p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside

There total 12 articles about p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside 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: 81.0%

p-vinylbenzylamine (50325-49-0) + p-(2-carboxyethyl)phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside (359687-05-1) → p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside (359687-25-5)

Guidance literature:

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1081/CAR-100103953

Reference yield:

3-(4-hydroxyphenyl)propionic acid benzyl ester (31770-76-0) → p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside (359687-25-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 59 percent / SnCl₄ / CH₂Cl₂ / 1 h / -19 °C

2.1: 74 percent / NaOBn / phenylmethanol / 1 h / 0 °C / pH 11

3.1: (Bu₃Sn)2O / toluene / 2 h / Heating

3.2: 66 percent / toluene / 72 h / 20 °C

4.1: 145 mg / pyridine / 4 h / 20 °C

5.1: 92 percent / 18-crown-6 / benzene / 4 h / 20 °C

6.1: 96 percent / tetrabutylammonium azide / hexane / 20 °C / ultrasonication

7.1: H₂ / Pd/C / benzene / 1 h

8.1: 311 mg / 0.5 h / 20 °C

9.1: 91 percent / H₂ / Pd(OH)2 / ethanol / 1 h

10.1: 81 percent / WSC / CH₂Cl₂ / 1 h / 0 °C

With pyridine; 18-crown-6 ether; hydrogen; tetrabutylammoniun azide; tin(IV) chloride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium phenyl-methanolate; bis(tri-n-butyltin)oxide; palladium dihydroxide; palladium on activated charcoal; In ethanol; hexane; dichloromethane; toluene; benzyl alcohol; benzene;

DOI:10.1081/CAR-100103953

Reference yield:

4-hydroxyphenylpropionic acid (501-97-3) → p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside (359687-25-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 765 mg / KHCO₃ / dimethylformamide / 12 h / 20 °C

2.1: 59 percent / SnCl₄ / CH₂Cl₂ / 1 h / -19 °C

3.1: 74 percent / NaOBn / phenylmethanol / 1 h / 0 °C / pH 11

4.1: (Bu₃Sn)2O / toluene / 2 h / Heating

4.2: 66 percent / toluene / 72 h / 20 °C

5.1: 145 mg / pyridine / 4 h / 20 °C

6.1: 92 percent / 18-crown-6 / benzene / 4 h / 20 °C

7.1: 96 percent / tetrabutylammonium azide / hexane / 20 °C / ultrasonication

8.1: H₂ / Pd/C / benzene / 1 h

9.1: 311 mg / 0.5 h / 20 °C

10.1: 91 percent / H₂ / Pd(OH)2 / ethanol / 1 h

11.1: 81 percent / WSC / CH₂Cl₂ / 1 h / 0 °C

With pyridine; 18-crown-6 ether; hydrogen; tetrabutylammoniun azide; tin(IV) chloride; potassium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium phenyl-methanolate; bis(tri-n-butyltin)oxide; palladium dihydroxide; palladium on activated charcoal; In ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzyl alcohol; benzene;

DOI:10.1081/CAR-100103953

upstream raw materials:

p-vinylbenzylamine

p-(2-carboxyethyl)phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside

4-hydroxyphenylpropionic acid

3-(4-hydroxyphenyl)propionic acid benzyl ester

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