2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-2-O-pivaloyl-α-D-rhamnopyranoside

Base Information

Chemical Name:2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-2-O-pivaloyl-α-D-rhamnopyranoside
CAS No.:798557-16-1
Molecular Formula:C₃₃H₃₈O₈
Molecular Weight:562.66
Hs Code.:

Synonyms:2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-2-O-pivaloyl-α-D-rhamnopyranoside

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Chemical Property of 2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-2-O-pivaloyl-α-D-rhamnopyranoside

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Technology Process of 2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-2-O-pivaloyl-α-D-rhamnopyranoside

There total 7 articles about 2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-2-O-pivaloyl-α-D-rhamnopyranoside 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: 94.0%

: 798557-35-4
2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-6-deoxy-3-O-p-methoxybenzyl-2-O-pivaloyl-α-D-rhamnopyranoside

: 798557-16-1
2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-2-O-pivaloyl-α-D-rhamnopyranoside

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃; for 0.666667h;
DOI:10.1021/ol048648u

Reference yield:

: 3282-30-2
pivaloyl chloride

: 798557-16-1
2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-2-O-pivaloyl-α-D-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 89 percent / DMAP; Et₃N / CH₂Cl₂ / 3.5 h / 0 °C

2.1: BH₃; Bu₂BOTf / tetrahydrofuran / 3 h / 0 °C

2.2: 93 percent / Et₃N / tetrahydrofuran / 1 h

3.1: 89 percent / PPh₃; imidazole; I₂ / toluene / 2 h / Heating

4.1: 91 percent / n-Bu₃SnH; AIBN / toluene / 2 h / Heating

5.1: 94 percent / DDQ / CH₂Cl₂; H₂O / 0.67 h / 0 °C

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); di-n-butylboryl trifluoromethanesulfonate; borane; iodine; tri-n-butyl-tin hydride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1021/ol048648u

Reference yield:

: 365535-43-9
2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-α-D-mannopyranoside

: 798557-16-1
2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-2-O-pivaloyl-α-D-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: Bu₂SnO / methanol / 1 h / 60 °C

1.2: 83 percent / Bu₄NI / dimethylformamide / 1.5 h / 90 °C

2.1: 89 percent / DMAP; Et₃N / CH₂Cl₂ / 3.5 h / 0 °C

3.1: BH₃; Bu₂BOTf / tetrahydrofuran / 3 h / 0 °C

3.2: 93 percent / Et₃N / tetrahydrofuran / 1 h

4.1: 89 percent / PPh₃; imidazole; I₂ / toluene / 2 h / Heating

5.1: 91 percent / n-Bu₃SnH; AIBN / toluene / 2 h / Heating

6.1: 94 percent / DDQ / CH₂Cl₂; H₂O / 0.67 h / 0 °C

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); di-n-butylboryl trifluoromethanesulfonate; borane; iodine; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1021/ol048648u