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

Base Information

Chemical Name:p-[2-(benzyloxycarbonyl)ethyl]phenyl 4-O-acetyl-2-deoxy-3,6-di-O-pivaloyl-β-D-arabino-hexopyranoside
CAS No.:359686-81-0
Molecular Formula:C₃₄H₄₄O₁₀
Molecular Weight:612.717
Hs Code.:

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

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

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

There total 9 articles about p-[2-(benzyloxycarbonyl)ethyl]phenyl 4-O-acetyl-2-deoxy-3,6-di-O-pivaloyl-β-D-arabino-hexopyranoside 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: 52.0%

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

: 359686-81-0
p-[2-(benzyloxycarbonyl)ethyl]phenyl 4-O-acetyl-2-deoxy-3,6-di-O-pivaloyl-β-D-arabino-hexopyranoside

Guidance literature:: With tetrabutylammonium borohydride; In benzene; for 29h; ultrasonication;
DOI:10.1081/CAR-100103953

Reference yield:

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

: 359686-81-0
p-[2-(benzyloxycarbonyl)ethyl]phenyl 4-O-acetyl-2-deoxy-3,6-di-O-pivaloyl-β-D-arabino-hexopyranoside

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: 52 percent / tetrabutylammonium tetrahydroborate / benzene / 29 h / ultrasonication

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

Reference yield:

: 501-97-3
4-hydroxyphenylpropionic acid

: 359686-81-0
p-[2-(benzyloxycarbonyl)ethyl]phenyl 4-O-acetyl-2-deoxy-3,6-di-O-pivaloyl-β-D-arabino-hexopyranoside

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: 52 percent / tetrabutylammonium tetrahydroborate / benzene / 29 h / ultrasonication

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