5-(Benzyloxy)-4-<(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)oxy>-3-(trifluoroacetyl)-N-<<2-(trimethylsilyl)ethoxy>methyl>indole

Base Information

Chemical Name:5-(Benzyloxy)-4-<(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)oxy>-3-(trifluoroacetyl)-N-<<2-(trimethylsilyl)ethoxy>methyl>indole
CAS No.:147624-42-8
Molecular Formula:C₅₀H₅₄F₃NO₉Si
Molecular Weight:898.061
Hs Code.:

Synonyms:5-(Benzyloxy)-4-<(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)oxy>-3-(trifluoroacetyl)-N-<<2-(trimethylsilyl)ethoxy>methyl>indole

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Chemical Property of 5-(Benzyloxy)-4-<(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)oxy>-3-(trifluoroacetyl)-N-<<2-(trimethylsilyl)ethoxy>methyl>indole

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Technology Process of 5-(Benzyloxy)-4-<(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)oxy>-3-(trifluoroacetyl)-N-<<2-(trimethylsilyl)ethoxy>methyl>indole

There total 9 articles about 5-(Benzyloxy)-4-<(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)oxy>-3-(trifluoroacetyl)-N-<<2-(trimethylsilyl)ethoxy>methyl>indole 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: 75.0%

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 147624-39-3
5-(Benzyloxy)-4-<(3,4,6-tri-O-benzyl-2-O-(trifluoroacetyl)-β-D-glucopyranosyl)oxy>-3-(trifluoroacetyl)indole

: 147624-42-8
5-(Benzyloxy)-4-<(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)oxy>-3-(trifluoroacetyl)-N-<<2-(trimethylsilyl)ethoxy>methyl>indole

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 5 ℃; for 0.5h;
DOI:10.1021/jo00062a034

Reference yield:

: 5779-91-9
2,3-bis(benzyloxy)benzaldehyde

: 147624-42-8
5-(Benzyloxy)-4-<(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)oxy>-3-(trifluoroacetyl)-N-<<2-(trimethylsilyl)ethoxy>methyl>indole

Guidance literature:: Multi-step reaction with 9 steps

1: 26 percent / fuming HNO₃ / acetic acid / 3 h / Ambient temperature

2: 70 percent / MgBr₂-Et₂O / benzene; diethyl ether / 12 h / Heating

3: 95 percent / sodium acetate / 0.75 h / 60 °C

4: N-methylmorpholine, KF, 18-crown-6 / 12 h / 10 °C

5: acetic anhydride, sodium acetate / 1 h / 60 °C

6: 64 percent / silica gel, reduced iron powder, glacial AcOH / toluene / 0.17 h / 90 °C

7: 1.) Na₂S₂O₄, 1.25 N NaOH, 2.) 15-crown-5 / 1.) DMF, water, 5 deg C, 15 min, 2.) DMF, H₂O, r.t., overnight

8: 83 percent / dimethylformamide / 1 h / 5 °C

9: 75 percent / NaH / tetrahydrofuran / 0.5 h / 5 °C

With 4-methyl-morpholine; potassium fluoride; sodium hydroxide; sodium dithionite; 15-crown-5; 18-crown-6 ether; nitric acid; sodium acetate; acetic anhydride; silica gel; iron; sodium hydride; acetic acid; magnesium bromide; In tetrahydrofuran; diethyl ether; acetic acid; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jo00062a034

Reference yield:

: 147624-33-7
3-(Benzyloxy)-2-hydroxy-6-nitrobenzaldehyde

: 147624-42-8
5-(Benzyloxy)-4-<(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)oxy>-3-(trifluoroacetyl)-N-<<2-(trimethylsilyl)ethoxy>methyl>indole

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / sodium acetate / 0.75 h / 60 °C

2: N-methylmorpholine, KF, 18-crown-6 / 12 h / 10 °C

3: acetic anhydride, sodium acetate / 1 h / 60 °C

4: 64 percent / silica gel, reduced iron powder, glacial AcOH / toluene / 0.17 h / 90 °C

5: 1.) Na₂S₂O₄, 1.25 N NaOH, 2.) 15-crown-5 / 1.) DMF, water, 5 deg C, 15 min, 2.) DMF, H₂O, r.t., overnight

6: 83 percent / dimethylformamide / 1 h / 5 °C

7: 75 percent / NaH / tetrahydrofuran / 0.5 h / 5 °C

With 4-methyl-morpholine; potassium fluoride; sodium hydroxide; sodium dithionite; 15-crown-5; 18-crown-6 ether; sodium acetate; acetic anhydride; silica gel; iron; sodium hydride; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00062a034