Dimethyl (3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranos-6-yl)malonate

Base Information

Chemical Name:Dimethyl (3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranos-6-yl)malonate
CAS No.:360562-11-4
Molecular Formula:C₂₁H₂₈O₉
Molecular Weight:424.448
Hs Code.:

Synonyms:Dimethyl (3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranos-6-yl)malonate

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Chemical Property of Dimethyl (3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranos-6-yl)malonate

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Technology Process of Dimethyl (3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranos-6-yl)malonate

There total 1 articles about Dimethyl (3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranos-6-yl)malonate 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: 67.0%

: 158946-12-4
3-O-benzyl 1,2-O-isopropylidene-5,6-O-sulfuryl-α-D-glucofuranose

: 108-59-8
malonic acid dimethyl ester

: Methyl 5-(3-O-benzyl-1,2-O-isopropylidene-α-D-erythrofuranos-4-yl)-2-oxotetrahydrofuran-3-carboxylate

: 360562-11-4
Dimethyl (3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranos-6-yl)malonate

Guidance literature:: malonic acid dimethyl ester; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h;

3-O-benzyl 1,2-O-isopropylidene-5,6-O-sulfuryl-α-D-glucofuranose; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

With sulfuric acid; In dichloromethane; at 20 ℃; for 15h;
DOI:10.1135/cccc20010785

Reference yield:

: 360562-11-4
Dimethyl (3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranos-6-yl)malonate

: Methyl 5-(3-O-benzyl-1,2-O-isopropylidene-α-D-erythrofuranos-4-yl)-2-oxotetrahydrofuran-3-carboxylate

Guidance literature:: With sodium methylate; In methanol; at 20 ℃;
DOI:10.1135/cccc20010785

Reference yield:

: 360562-11-4
Dimethyl (3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranos-6-yl)malonate

: (1R,2S,4R)-5,5-Bis(hydroxymethyl)cyclohexane-1,2,4-diol

Guidance literature:: Multi-step reaction with 8 steps

1.1: MeONa / methanol / 20 °C

2.1: Dowex 50(H(+)); H₂O / dioxane / 6 h / 80 °C

2.2: aq. NaIO₄ / dioxane

2.3: 35 percent / pyridine / 48 h / 20 °C

3.1: 79 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

4.1: 93 percent / pyridine / 50 h / 20 °C

5.1: 91 percent / H₂ / 10 percent Pd/C / methanol; dimethylformamide / 45 h

6.1: NaH / dimethylformamide / 0.5 h / 0 °C

6.2: 90 percent / dimethylformamide / 1 h / 0 - 20 °C

7.1: 82 percent / Bu₃SnH; AIBN / toluene / 0.5 h / Heating

8.1: 94 percent / NaOMe / methanol / 20 °C

With pyridine; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); Dowex 50(H(+)); water; hydrogen; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene;
DOI:10.1135/cccc20010785