2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-6-deoxy-3-O-p-methoxybenzyl-6-iodo-2-O-pivaloyl-α-D-mannopyranoside

Base Information

Chemical Name:2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-6-deoxy-3-O-p-methoxybenzyl-6-iodo-2-O-pivaloyl-α-D-mannopyranoside
CAS No.:798557-34-3
Molecular Formula:C₄₁H₄₅IO₉
Molecular Weight:808.707
Hs Code.:

Synonyms:2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-6-deoxy-3-O-p-methoxybenzyl-6-iodo-2-O-pivaloyl-α-D-mannopyranoside

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Chemical Property of 2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-6-deoxy-3-O-p-methoxybenzyl-6-iodo-2-O-pivaloyl-α-D-mannopyranoside

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Technology Process of 2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-6-deoxy-3-O-p-methoxybenzyl-6-iodo-2-O-pivaloyl-α-D-mannopyranoside

There total 6 articles about 2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-6-deoxy-3-O-p-methoxybenzyl-6-iodo-2-O-pivaloyl-α-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: 89.0%

: 798557-33-2
2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-3-O-p-methoxybenzyl-2-O-pivaloyl-α-D-mannopyranoside

: 798557-34-3
2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-6-deoxy-3-O-p-methoxybenzyl-6-iodo-2-O-pivaloyl-α-D-mannopyranoside

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In toluene; for 2h; Heating;
DOI:10.1021/ol048648u

Reference yield:

: 3282-30-2
pivaloyl chloride

: 798557-34-3
2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-6-deoxy-3-O-p-methoxybenzyl-6-iodo-2-O-pivaloyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 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

With 1H-imidazole; dmap; di-n-butylboryl trifluoromethanesulfonate; borane; iodine; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ol048648u

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 798557-34-3
2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-6-deoxy-3-O-p-methoxybenzyl-6-iodo-2-O-pivaloyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; dmap; di-n-butylboryl trifluoromethanesulfonate; borane; iodine; di(n-butyl)tin oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1021/ol048648u