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

Base Information

Chemical Name:p-[2-(benzyloxycarbonyl)ethyl]phenyl 4-O-acetyl-2-azido-2-deoxy-3,6-di-O-pivaloyl-β-D-mannopyranoside
CAS No.:359686-74-1
Molecular Formula:C₃₄H₄₃N₃O₁₀
Molecular Weight:653.73
Hs Code.:

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

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

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

There total 9 articles about p-[2-(benzyloxycarbonyl)ethyl]phenyl 4-O-acetyl-2-azido-2-deoxy-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: 96.0%

: 359686-69-4
p-[2-(benzyloxycarbonyl)ethyl]phenyl 4-O-acetyl-3,6-di-O-pivaloyl-2-O-trifluoromethylsulfonyl-β-D-glucopyranoside

: 359686-74-1
p-[2-(benzyloxycarbonyl)ethyl]phenyl 4-O-acetyl-2-azido-2-deoxy-3,6-di-O-pivaloyl-β-D-mannopyranoside

Guidance literature:: With tetrabutylammoniun azide; In hexane; at 20 ℃; ultrasonication;
DOI:10.1081/CAR-100103953

Reference yield:

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

: 359686-74-1
p-[2-(benzyloxycarbonyl)ethyl]phenyl 4-O-acetyl-2-azido-2-deoxy-3,6-di-O-pivaloyl-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 501-97-3
4-hydroxyphenylpropionic acid

: 359686-74-1
p-[2-(benzyloxycarbonyl)ethyl]phenyl 4-O-acetyl-2-azido-2-deoxy-3,6-di-O-pivaloyl-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 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

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