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

Base Information

Chemical Name:(2-methyl-5-tert-butylphenyl)-4,6-di-O-benzyl-3-O-fluorenylmethoxycarbonyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside
CAS No.:1456773-47-9
Molecular Formula:C₅₁H₅₆O₈S
Molecular Weight:829.067
Hs Code.:

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

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

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

There total 10 articles about (2-methyl-5-tert-butylphenyl)-4,6-di-O-benzyl-3-O-fluorenylmethoxycarbonyl-2-O-pivaloyl-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: 91.0%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 1456773-46-8
(2-methyl-5-tert-butylphenyl)-4,6-di-O-benzyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

: 1456773-47-9
(2-methyl-5-tert-butylphenyl)-4,6-di-O-benzyl-3-O-fluorenylmethoxycarbonyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

Guidance literature:: With pyridine; In dichloromethane; Inert atmosphere;
DOI:10.1002/chem.201204518

Reference yield:

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

: 1456773-47-9
(2-methyl-5-tert-butylphenyl)-4,6-di-O-benzyl-3-O-fluorenylmethoxycarbonyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: boron trifluoride diethyl etherate / dichloromethane / Inert atmosphere

2: sodium methylate / methanol / Inert atmosphere

3: 10-camphorsulfonic acid / acetonitrile / Inert atmosphere

4: 1H-imidazole / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

5: pyridine; dmap / 0 - 80 °C / Inert atmosphere

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

7: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere

8: tetrabutyl ammonium fluoride; acetic acid / N,N-dimethyl-formamide / 0 - 35 °C / Inert atmosphere

9: pyridine / dichloromethane / Inert atmosphere

With pyridine; 1H-imidazole; dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; acetic acid; 10-camphorsulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/chem.201204518

Reference yield:

: 1456773-45-7
(2-methyl-5-tert-butylphenyl)-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

: 1456773-47-9
(2-methyl-5-tert-butylphenyl)-4,6-di-O-benzyl-3-O-fluorenylmethoxycarbonyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride; acetic acid / N,N-dimethyl-formamide / 0 - 35 °C / Inert atmosphere

2: pyridine / dichloromethane / Inert atmosphere

With pyridine; tetrabutyl ammonium fluoride; acetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.201204518