1-O-acetyl-2,6-anhydro-4-O-benzyl-5-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol

Base Information

Chemical Name:1-O-acetyl-2,6-anhydro-4-O-benzyl-5-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol
CAS No.:1393360-80-9
Molecular Formula:C₄₀H₄₈O₈Si
Molecular Weight:684.902
Hs Code.:

Synonyms:1-O-acetyl-2,6-anhydro-4-O-benzyl-5-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol

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Chemical Property of 1-O-acetyl-2,6-anhydro-4-O-benzyl-5-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol

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Technology Process of 1-O-acetyl-2,6-anhydro-4-O-benzyl-5-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol

There total 7 articles about 1-O-acetyl-2,6-anhydro-4-O-benzyl-5-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol 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: 85.0%

: 1393360-78-5
3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-1-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol

: 1393360-80-9
1-O-acetyl-2,6-anhydro-4-O-benzyl-5-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol

Guidance literature:: 3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-1-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol; With 2,6-di-tert-butyl-4-methylpyridine; borane-THF; In dichloromethane; at -20 ℃; for 0.25h; Inert atmosphere;

With di-n-butylboryl trifluoromethanesulfonate; In dichloromethane; at -20 - 0 ℃; for 2.16667h; Inert atmosphere;

With triethylamine; In dichloromethane; at -20 ℃; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2012.04.001

Reference yield:

: 1393360-75-2
3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-1-O-triethylsilyl-D-glycero-D-gulo-heptitol

: 1393360-80-9
1-O-acetyl-2,6-anhydro-4-O-benzyl-5-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 6 h / 20 °C / Inert atmosphere

3.1: 2,6-di-tert-butyl-4-methylpyridine; borane-THF / dichloromethane / 0.25 h / -20 °C / Inert atmosphere

3.2: 2.17 h / -20 - 0 °C / Inert atmosphere

3.3: -20 °C / Inert atmosphere

With 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; borane-THF; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2012.04.001

Reference yield:

: 3-O-benzyl-4,6-O-p-methoxybenzylidene-D-glucopyranose

: 1393360-80-9
1-O-acetyl-2,6-anhydro-4-O-benzyl-5-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine / dichloromethane / 20 °C / Inert atmosphere

2.1: dicobalt octacarbonyl / 0.5 h / 20 °C

2.2: 48 h / 50 °C

3.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

4.1: 1H-imidazole / dichloromethane / 6 h / 20 °C / Inert atmosphere

5.1: 2,6-di-tert-butyl-4-methylpyridine; borane-THF / dichloromethane / 0.25 h / -20 °C / Inert atmosphere

5.2: 2.17 h / -20 - 0 °C / Inert atmosphere

5.3: -20 °C / Inert atmosphere

With pyridine; 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; dicobalt octacarbonyl; borane-THF; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2012.04.001