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

Base Information

• Chemical Name: p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 4-O-acetyl-2-deoxy-2-fluoro-3,6-di-O-pivaloyl-β-D-mannopyranoside
• CAS No.: 359687-32-4
• Molecular Formula: C₃₆H₄₆FNO₉
• Molecular Weight: 655.761

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

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

There total 10 articles about p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 4-O-acetyl-2-deoxy-2-fluoro-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: 61.0%

p-vinylbenzylamine (50325-49-0) + p-(2-carboxyethyl)phenyl 4-O-acetyl-2-deoxy-2-fluoro-3,6-di-O-pivaloyl-β-D-mannopyranoside (359687-15-3) → p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 4-O-acetyl-2-deoxy-2-fluoro-3,6-di-O-pivaloyl-β-D-mannopyranoside (359687-32-4)

Guidance literature:

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 0 ℃; for 0.333333h;

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 4-O-acetyl-2-deoxy-2-fluoro-3,6-di-O-pivaloyl-β-D-mannopyranoside (359687-32-4)

Guidance literature:

Multi-step reaction with 8 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: 87 percent / 18-crown-6 / benzene / 12 h / ultrasonication

6.1: 95 percent / H₂ / Pd(OH)2 / ethanol / 2 h

7.1: 90 percent / H₂ / Pd(OH)2 / ethanol / 1 h

8.1: 61 percent / WSC / CH₂Cl₂ / 0.33 h / 0 °C

With pyridine; 18-crown-6 ether; hydrogen; tin(IV) chloride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium phenyl-methanolate; bis(tri-n-butyltin)oxide; palladium dihydroxide; In ethanol; 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 4-O-acetyl-2-deoxy-2-fluoro-3,6-di-O-pivaloyl-β-D-mannopyranoside (359687-32-4)

Guidance literature:

Multi-step reaction with 9 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: 87 percent / 18-crown-6 / benzene / 12 h / ultrasonication

7.1: 95 percent / H₂ / Pd(OH)2 / ethanol / 2 h

8.1: 90 percent / H₂ / Pd(OH)2 / ethanol / 1 h

9.1: 61 percent / WSC / CH₂Cl₂ / 0.33 h / 0 °C

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

DOI:10.1081/CAR-100103953

upstream raw materials:

p-vinylbenzylamine

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

4-hydroxyphenylpropionic acid

3-(4-hydroxyphenyl)propionic acid benzyl ester

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