3-O-benzyl-1,6-O-diacetyl-4-O-tert-butyldiphenylsilyl-β-L-glucopyranose

Base Information

Chemical Name:3-O-benzyl-1,6-O-diacetyl-4-O-tert-butyldiphenylsilyl-β-L-glucopyranose
CAS No.:1393360-86-5
Molecular Formula:C₃₃H₄₀O₈Si
Molecular Weight:592.761
Hs Code.:

Synonyms:3-O-benzyl-1,6-O-diacetyl-4-O-tert-butyldiphenylsilyl-β-L-glucopyranose

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Chemical Property of 3-O-benzyl-1,6-O-diacetyl-4-O-tert-butyldiphenylsilyl-β-L-glucopyranose

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Technology Process of 3-O-benzyl-1,6-O-diacetyl-4-O-tert-butyldiphenylsilyl-β-L-glucopyranose

There total 11 articles about 3-O-benzyl-1,6-O-diacetyl-4-O-tert-butyldiphenylsilyl-β-L-glucopyranose 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: 96.0%

: 1393360-84-3
3-O-benzyl-1,6-O-diacetyl-2-O-(p-methoxybenzyl)-4-O-tert-butyldiphenylsilyl-β-L-glucopyranose

: 1393360-86-5
3-O-benzyl-1,6-O-diacetyl-4-O-tert-butyldiphenylsilyl-β-L-glucopyranose

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at -20 ℃; for 2h; chemoselective reaction;
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

: 1393360-86-5
3-O-benzyl-1,6-O-diacetyl-4-O-tert-butyldiphenylsilyl-β-L-glucopyranose

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 50 °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

4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 4 h / 20 °C

5.1: pyridine / benzene / Inert atmosphere; Reflux

6.1: trifluoroacetic acid / dichloromethane / 2 h / -20 °C

With pyridine; 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; borane-THF; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; acetic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/j.tet.2012.04.001

Reference yield:

: 1393360-79-6
1-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-3-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol

: 1393360-86-5
3-O-benzyl-1,6-O-diacetyl-4-O-tert-butyldiphenylsilyl-β-L-glucopyranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-di-tert-butyl-4-methylpyridine; borane-THF / dichloromethane / 0.25 h / -20 °C / Inert atmosphere

1.2: 2.17 h / -20 - 0 °C / Inert atmosphere

1.3: -20 °C / Inert atmosphere

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 4 h / 20 °C

3.1: pyridine / benzene / Inert atmosphere; Reflux

4.1: trifluoroacetic acid / dichloromethane / 2 h / -20 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; borane-THF; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; trifluoroacetic acid; In dichloromethane; water; benzene;
DOI:10.1016/j.tet.2012.04.001