2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-C-methyl-α-D-manno-hexopyranoside

Base Information

Chemical Name:2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-C-methyl-α-D-manno-hexopyranoside
CAS No.:798557-14-9
Molecular Formula:C₂₉H₃₀O₈
Molecular Weight:506.552
Hs Code.:

Synonyms:2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-C-methyl-α-D-manno-hexopyranoside

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Chemical Property of 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-C-methyl-α-D-manno-hexopyranoside

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Technology Process of 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-C-methyl-α-D-manno-hexopyranoside

There total 8 articles about 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-C-methyl-α-D-manno-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: 82.0%

: 798557-27-4
2''-(benzyloxycarbonyl)benzyl 3,3'-anhydro-4,6-O-benzylidene-3-C-hydroxymethyl-α-D-manno-hexopyranoside

: 798557-14-9
2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-C-methyl-α-D-manno-hexopyranoside

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium iodide; In 1,2-dimethoxyethane; at 90 ℃; for 4h;
DOI:10.1021/ol048648u

Reference yield:

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

: 798557-14-9
2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-C-methyl-α-D-manno-hexopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: Bu₂SnO / methanol / 1 h / 60 °C

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

2.1: 83 percent / imidazole / dimethylformamide / 5 h / 20 °C

3.1: 88 percent / DDQ / CH₂Cl₂; H₂O / 0.67 h / 0 °C

4.1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

5.1: 92 percent / n-BuLi / tetrahydrofuran / 5.5 h / 0 °C

6.1: 95 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

7.1: 80 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 4 h / 0 °C

8.1: 82 percent / NaI; n-Bu₃SnH; AIBN / 1,2-dimethoxy-ethane / 4 h / 90 °C

With 1H-imidazole; n-butyllithium; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Dess-Martin oxidation;
DOI:10.1021/ol048648u

Reference yield:

: 798557-26-3
2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-deoxy-3-methylene-α-D-arabino-hexopyranoside

: 798557-14-9
2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-C-methyl-α-D-manno-hexopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 4 h / 0 °C

2: 82 percent / NaI; n-Bu₃SnH; AIBN / 1,2-dimethoxy-ethane / 4 h / 90 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/ol048648u