(2-methyl-5-tert-butylphenyl) 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:(2-methyl-5-tert-butylphenyl) 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside
CAS No.:1421767-99-8
Molecular Formula:C₄₄H₅₆O₆SSi
Molecular Weight:741.077
Hs Code.:

Synonyms:(2-methyl-5-tert-butylphenyl) 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

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Chemical Property of (2-methyl-5-tert-butylphenyl) 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

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Technology Process of (2-methyl-5-tert-butylphenyl) 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

There total 9 articles about (2-methyl-5-tert-butylphenyl) 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-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: 94.0%

: 1421767-98-7
2-methyl-5-tert-butylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

: 100-39-0
benzyl bromide

: 1421767-99-8
(2-methyl-5-tert-butylphenyl) 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

Guidance literature:: With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20 ℃; for 4h; Inert atmosphere;
DOI:10.1016/j.carres.2019.06.014

Reference yield:

: 7340-90-1
2-methyl-5-tert-butylthiophenol

: 1421767-99-8
(2-methyl-5-tert-butylphenyl) 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: boron trifluoride diethyl etherate / dichloromethane / Inert atmosphere

2: sodium methylate / methanol / Inert atmosphere

3: camphor-10-sulfonic acid / acetonitrile / 2.5 h / 20 °C / Inert atmosphere

4: 1H-imidazole / N,N-dimethyl-formamide / 4 h / Inert atmosphere

5: pyridine; dmap / 12 h / 0 - 70 °C / Inert atmosphere

6: trimethylsilyl trifluoromethanesulfonate; borane-THF / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

7: sodium hydride / N,N-dimethyl-formamide; tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

: 604-69-3
β-D-glucose pentaacetate

: 1421767-99-8
(2-methyl-5-tert-butylphenyl) 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: boron trifluoride diethyl etherate / dichloromethane / Inert atmosphere

2: sodium methylate / methanol / Inert atmosphere

3: camphor-10-sulfonic acid / acetonitrile / 2.5 h / 20 °C / Inert atmosphere

4: 1H-imidazole / N,N-dimethyl-formamide / 4 h / Inert atmosphere

5: pyridine; dmap / 12 h / 0 - 70 °C / Inert atmosphere

6: trimethylsilyl trifluoromethanesulfonate; borane-THF / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

7: sodium hydride / N,N-dimethyl-formamide; tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;