3-(4-methoxy-4-oxobutanoyl)-2-nitrophenyl tetra-O-acetyl-β-D-glucopyranoside

Base Information

Chemical Name:3-(4-methoxy-4-oxobutanoyl)-2-nitrophenyl tetra-O-acetyl-β-D-glucopyranoside
CAS No.:289665-42-5
Molecular Formula:C₂₅H₂₉NO₁₅
Molecular Weight:583.503
Hs Code.:

Synonyms:3-(4-methoxy-4-oxobutanoyl)-2-nitrophenyl tetra-O-acetyl-β-D-glucopyranoside

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Chemical Property of 3-(4-methoxy-4-oxobutanoyl)-2-nitrophenyl tetra-O-acetyl-β-D-glucopyranoside

Chemical Property:

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Technology Process of 3-(4-methoxy-4-oxobutanoyl)-2-nitrophenyl tetra-O-acetyl-β-D-glucopyranoside

There total 6 articles about 3-(4-methoxy-4-oxobutanoyl)-2-nitrophenyl tetra-O-acetyl-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:

: 289665-41-4
methyl 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoate

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 289665-42-5
3-(4-methoxy-4-oxobutanoyl)-2-nitrophenyl tetra-O-acetyl-β-D-glucopyranoside

Guidance literature:: With silver imidazolate; zinc(II) chloride; In diethyl ether; dichloromethane; at 20 ℃; for 16h;
DOI:10.1016/S0040-4020(00)00285-4

Reference yield:

: 53055-05-3
3-methoxy 2-nitrobenzaldehyde

: 289665-42-5
3-(4-methoxy-4-oxobutanoyl)-2-nitrophenyl tetra-O-acetyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 92 percent / TiCl₄ / CH₂Cl₂ / 0.17 h / 20 °C

2.1: BH₃*THF; cyclohexene / tetrahydrofuran / 0.5 h / 0 - 20 °C

2.2: 75 percent / 3.0 M NaOH; aq. H₂O₂ / 0.25 h / 20 °C

3.1: 55 percent / CrO₃; aq. H₂SO₄ / acetone / 0.5 h

4.1: LiCl / dimethylformamide; H₂O / 4 h / Heating

5.1: 208 mg / BF₃*OEt₂ / 1 h / Heating

6.1: 83 percent Turnov_. / silver imidazolate; ZnCl₂ / CH₂Cl₂; diethyl ether / 16 h / 20 °C

With chromium(VI) oxide; borane-THF; silver imidazolate; sulfuric acid; boron trifluoride diethyl etherate; titanium tetrachloride; lithium chloride; zinc(II) chloride; cyclohexene; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1.1: allylation / 2.1: hydroboration / 2.2: Oxidation / 3.1: Oxidation / 4.1: Substitution / 5.1: Methylation / 6.1: glycosylation;
DOI:10.1016/S0040-4020(00)00285-4

Reference yield:

: 103646-41-9
4-(3-methoxy-2-nitrophenyl)-4-oxobutanoic acid

: 289665-42-5
3-(4-methoxy-4-oxobutanoyl)-2-nitrophenyl tetra-O-acetyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: LiCl / dimethylformamide; H₂O / 4 h / Heating

2: 208 mg / BF₃*OEt₂ / 1 h / Heating

3: 83 percent Turnov_. / silver imidazolate; ZnCl₂ / CH₂Cl₂; diethyl ether / 16 h / 20 °C

With silver imidazolate; boron trifluoride diethyl etherate; lithium chloride; zinc(II) chloride; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 1: Substitution / 2: Methylation / 3: glycosylation;
DOI:10.1016/S0040-4020(00)00285-4