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

Base Information

Chemical Name:p-[2-(benzyloxycarbonyl)ethyl]phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside
CAS No.:359686-95-6
Molecular Formula:C₃₆H₄₇NO₁₁
Molecular Weight:669.769
Hs Code.:

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

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

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

There total 11 articles about p-[2-(benzyloxycarbonyl)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:

: 31770-76-0
3-(4-hydroxyphenyl)propionic acid benzyl ester

: 359686-95-6
p-[2-(benzyloxycarbonyl)ethyl]phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside

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: 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

With pyridine; 18-crown-6 ether; hydrogen; tetrabutylammoniun azide; tin(IV) chloride; sodium phenyl-methanolate; bis(tri-n-butyltin)oxide; palladium on activated charcoal; In hexane; dichloromethane; toluene; benzyl alcohol; benzene;
DOI:10.1081/CAR-100103953

Reference yield:

: 501-97-3
4-hydroxyphenylpropionic acid

: 359686-95-6
p-[2-(benzyloxycarbonyl)ethyl]phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside

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: 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

With pyridine; 18-crown-6 ether; hydrogen; tetrabutylammoniun azide; tin(IV) chloride; potassium hydrogencarbonate; sodium phenyl-methanolate; bis(tri-n-butyltin)oxide; palladium on activated charcoal; In hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzyl alcohol; benzene;
DOI:10.1081/CAR-100103953

Reference yield:

: 3282-30-2
pivaloyl chloride

: 359686-95-6
p-[2-(benzyloxycarbonyl)ethyl]phenyl 2-acetamido-2-deoxy-4-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

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

1.2: 66 percent / toluene / 72 h / 20 °C

2.1: 145 mg / pyridine / 4 h / 20 °C

3.1: 92 percent / 18-crown-6 / benzene / 4 h / 20 °C

4.1: 96 percent / tetrabutylammonium azide / hexane / 20 °C / ultrasonication

5.1: H₂ / Pd/C / benzene / 1 h

6.1: 311 mg / 0.5 h / 20 °C

With pyridine; 18-crown-6 ether; hydrogen; tetrabutylammoniun azide; bis(tri-n-butyltin)oxide; palladium on activated charcoal; In hexane; toluene; benzene;
DOI:10.1081/CAR-100103953