Methyl (2S,3R,4R)-2-(acetyloxy)-3-(benzyloxy)-4-(formyloxy)-7-oxo-6-oxabicyclo[3.2.1]octane-1-carboxylate

Base Information

Chemical Name:Methyl (2S,3R,4R)-2-(acetyloxy)-3-(benzyloxy)-4-(formyloxy)-7-oxo-6-oxabicyclo[3.2.1]octane-1-carboxylate
CAS No.:360562-13-6
Molecular Formula:C₁₉H₂₀O₉
Molecular Weight:392.362
Hs Code.:

Synonyms:Methyl (2S,3R,4R)-2-(acetyloxy)-3-(benzyloxy)-4-(formyloxy)-7-oxo-6-oxabicyclo[3.2.1]octane-1-carboxylate

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Chemical Property of Methyl (2S,3R,4R)-2-(acetyloxy)-3-(benzyloxy)-4-(formyloxy)-7-oxo-6-oxabicyclo[3.2.1]octane-1-carboxylate

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Technology Process of Methyl (2S,3R,4R)-2-(acetyloxy)-3-(benzyloxy)-4-(formyloxy)-7-oxo-6-oxabicyclo[3.2.1]octane-1-carboxylate

There total 4 articles about Methyl (2S,3R,4R)-2-(acetyloxy)-3-(benzyloxy)-4-(formyloxy)-7-oxo-6-oxabicyclo[3.2.1]octane-1-carboxylate 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: 35.0%

: 108-24-7
acetic anhydride

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

: 360562-13-6
Methyl (2S,3R,4R)-2-(acetyloxy)-3-(benzyloxy)-4-(formyloxy)-7-oxo-6-oxabicyclo[3.2.1]octane-1-carboxylate

: Methyl (2R,3R,4R)-2-(acetyloxy)-3-(benzyloxy)-4-(formyloxy)-7-oxo-6-oxabicyclo[3.2.1]octane-1-carboxylate

Guidance literature:: Methyl 5-(3-O-benzyl-1,2-O-isopropylidene-α-D-erythrofuranos-4-yl)-2-oxotetrahydrofuran-3-carboxylate; With Dowex 50(H(+)); water; In 1,4-dioxane; at 80 ℃; for 6h;

With sodium periodate; In 1,4-dioxane;

acetic anhydride; With pyridine; at 20 ℃; for 48h;
DOI:10.1135/cccc20010785

Reference yield:

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

: 360562-13-6
Methyl (2S,3R,4R)-2-(acetyloxy)-3-(benzyloxy)-4-(formyloxy)-7-oxo-6-oxabicyclo[3.2.1]octane-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 0.25 h / 0 °C

1.2: dimethylformamide / 2 h / 20 °C

1.3: 67 percent / aq. H₂SO₄ / CH₂Cl₂ / 15 h / 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

With Dowex 50(H(+)); water; sodium hydride; In 1,4-dioxane; N,N-dimethyl-formamide;
DOI:10.1135/cccc20010785

Reference yield:

: 108-59-8
malonic acid dimethyl ester

: 360562-13-6
Methyl (2S,3R,4R)-2-(acetyloxy)-3-(benzyloxy)-4-(formyloxy)-7-oxo-6-oxabicyclo[3.2.1]octane-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 0.25 h / 0 °C

1.2: dimethylformamide / 2 h / 20 °C

1.3: 67 percent / aq. H₂SO₄ / CH₂Cl₂ / 15 h / 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

With Dowex 50(H(+)); water; sodium hydride; In 1,4-dioxane; N,N-dimethyl-formamide;
DOI:10.1135/cccc20010785