methyl 2-azido-2-deoxy-3-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2',6-di-O-(methane-1,2-diyl)-β-D-glucopyranoside

Base Information

Chemical Name:methyl 2-azido-2-deoxy-3-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2',6-di-O-(methane-1,2-diyl)-β-D-glucopyranoside
CAS No.:440345-51-7
Molecular Formula:C₄₂H₄₇N₃O₁₀
Molecular Weight:753.849
Hs Code.:

Synonyms:methyl 2-azido-2-deoxy-3-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2',6-di-O-(methane-1,2-diyl)-β-D-glucopyranoside

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Chemical Property of methyl 2-azido-2-deoxy-3-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2',6-di-O-(methane-1,2-diyl)-β-D-glucopyranoside

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Technology Process of methyl 2-azido-2-deoxy-3-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2',6-di-O-(methane-1,2-diyl)-β-D-glucopyranoside

There total 9 articles about methyl 2-azido-2-deoxy-3-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2',6-di-O-(methane-1,2-diyl)-β-D-glucopyranoside 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: 60.0%

: 3561-67-9
bis(phenylthio)methane

: 440345-50-6
methyl 2-azido-2-deoxy-3-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside

: 440345-51-7
methyl 2-azido-2-deoxy-3-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2',6-di-O-(methane-1,2-diyl)-β-D-glucopyranoside

Guidance literature:: bis(phenylthio)methane; methyl 2-azido-2-deoxy-3-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside; In dichloromethane; acetonitrile; at 20 ℃; for 1h;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; acetonitrile; at -35 ℃; for 2h; Further stages.;
DOI:10.1021/ja0169771

Reference yield:

: 440345-53-9
methyl 2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

: 440345-51-7
methyl 2-azido-2-deoxy-3-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2',6-di-O-(methane-1,2-diyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / imidazole / dimethylformamide / 2 h / 0 °C

2.1: 80 percent / BF₃*Et₂O / CH₂Cl₂ / 3 h / -40 °C

3.1: 95 percent / 48percent aq. tetrafluoroboric acid / acetonitrile / 0.08 h / 20 °C

4.1: 98 percent / NaOMe; MeOH / 48 h / 20 °C

5.1: CH₂Cl₂; acetonitrile / 1 h / 20 °C

5.2: 60 percent / N-iodosuccinimide; trifluoromethanesulfonic acid / acetonitrile; CH₂Cl₂ / 2 h / -35 °C

With 1H-imidazole; methanol; boron trifluoride diethyl etherate; sodium methylate; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja0169771

Reference yield:

: 440345-54-0
methyl 2-azido-3-O-benzyl-2-deoxy-4,6-O-benzylidine-D-glucopyranoside

: 440345-51-7
methyl 2-azido-2-deoxy-3-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2',6-di-O-(methane-1,2-diyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 85 percent / tetrafluoroboronic acid / CH₂Cl₂ / 1 h

2.1: 98 percent / imidazole / dimethylformamide / 2 h / 0 °C

3.1: 80 percent / BF₃*Et₂O / CH₂Cl₂ / 3 h / -40 °C

4.1: 95 percent / 48percent aq. tetrafluoroboric acid / acetonitrile / 0.08 h / 20 °C

5.1: 98 percent / NaOMe; MeOH / 48 h / 20 °C

6.1: CH₂Cl₂; acetonitrile / 1 h / 20 °C

6.2: 60 percent / N-iodosuccinimide; trifluoromethanesulfonic acid / acetonitrile; CH₂Cl₂ / 2 h / -35 °C

With 1H-imidazole; methanol; tetrafluoroboric acid; boron trifluoride diethyl etherate; sodium methylate; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja0169771