p-methoxyphenyl 4-O-benzoyl-6-bromo-2-O-tert-butyldimethylsilyl-3,6-dideoxy-β-D-ribo-hexopyranoside

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Chemical Name:p-methoxyphenyl 4-O-benzoyl-6-bromo-2-O-tert-butyldimethylsilyl-3,6-dideoxy-β-D-ribo-hexopyranoside
CAS No.:278784-73-9
Molecular Formula:C₂₆H₃₅BrO₆Si
Molecular Weight:551.55
Hs Code.:

Synonyms:p-methoxyphenyl 4-O-benzoyl-6-bromo-2-O-tert-butyldimethylsilyl-3,6-dideoxy-β-D-ribo-hexopyranoside

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Chemical Property of p-methoxyphenyl 4-O-benzoyl-6-bromo-2-O-tert-butyldimethylsilyl-3,6-dideoxy-β-D-ribo-hexopyranoside

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Technology Process of p-methoxyphenyl 4-O-benzoyl-6-bromo-2-O-tert-butyldimethylsilyl-3,6-dideoxy-β-D-ribo-hexopyranoside

There total 7 articles about p-methoxyphenyl 4-O-benzoyl-6-bromo-2-O-tert-butyldimethylsilyl-3,6-dideoxy-β-D-ribo-hexopyranoside 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: 93.0%

: p-methoxyphenyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-3-deoxy-β-D-ribo-hexopyranoside

: 278784-73-9
p-methoxyphenyl 4-O-benzoyl-6-bromo-2-O-tert-butyldimethylsilyl-3,6-dideoxy-β-D-ribo-hexopyranoside

Guidance literature:: With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; for 0.5h; Heating;
DOI:10.1021/jo991812k

Reference yield:

: 2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6
p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

: 278784-73-9
p-methoxyphenyl 4-O-benzoyl-6-bromo-2-O-tert-butyldimethylsilyl-3,6-dideoxy-β-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: MeONa / methanol / 2 h

2.1: p-TsOH / acetonitrile / Heating

3.1: 91 percent / SO₂Cl₂ / CH₂Cl₂; pyridine / 2 h / -78 - 20 °C

4.1: Et₄NBr / CH₂Cl₂ / 1 h / 20 °C

4.2: 96 percent / KHCO₃; KI / methanol; H₂O / 0.25 h

5.1: 91 percent / imidazole / dimethylformamide / 3 h / 60 °C

6.1: 87 percent / KHCO₃; H₂ / 10percent Pd/carbon / ethyl acetate; ethanol / 96 h / 760.05 Torr

7.1: 93 percent / NBS; BaCO₃ / CCl₄ / 0.5 h / Heating

With 1H-imidazole; N-Bromosuccinimide; sulfuryl dichloride; tetraethylammonium bromide; hydrogen; sodium methylate; potassium hydrogencarbonate; toluene-4-sulfonic acid; barium carbonate; 10percent Pd/carbon; In pyridine; methanol; tetrachloromethane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1.1: Deacetylation / 2.1: Condensation / 3.1: Substitution / 4.1: Substitution / 4.2: Hydrolysis / 5.1: silylation / 6.1: Dehalogenation / 7.1: Ring cleavage;
DOI:10.1021/jo991812k

Reference yield:

: 144367-31-7
4-methoxyphenyl 4,6-O-benzylidene-β-D-glucopyranoside

: 278784-73-9
p-methoxyphenyl 4-O-benzoyl-6-bromo-2-O-tert-butyldimethylsilyl-3,6-dideoxy-β-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / SO₂Cl₂ / CH₂Cl₂; pyridine / 2 h / -78 - 20 °C

2.1: Et₄NBr / CH₂Cl₂ / 1 h / 20 °C

2.2: 96 percent / KHCO₃; KI / methanol; H₂O / 0.25 h

3.1: 91 percent / imidazole / dimethylformamide / 3 h / 60 °C

4.1: 87 percent / KHCO₃; H₂ / 10percent Pd/carbon / ethyl acetate; ethanol / 96 h / 760.05 Torr

5.1: 93 percent / NBS; BaCO₃ / CCl₄ / 0.5 h / Heating

With 1H-imidazole; N-Bromosuccinimide; sulfuryl dichloride; tetraethylammonium bromide; hydrogen; potassium hydrogencarbonate; barium carbonate; 10percent Pd/carbon; In pyridine; tetrachloromethane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Substitution / 2.2: Hydrolysis / 3.1: silylation / 4.1: Dehalogenation / 5.1: Ring cleavage;
DOI:10.1021/jo991812k