(2S,3R,4R,5R)-2,3,5-Tris(benzoyloxy)-3-(benzyloxy)-1,1-bis[(benzoyloxy)methyl]cyclohexane

Base Information

Chemical Name:(2S,3R,4R,5R)-2,3,5-Tris(benzoyloxy)-3-(benzyloxy)-1,1-bis[(benzoyloxy)methyl]cyclohexane
CAS No.:360562-16-9
Molecular Formula:C₅₀H₄₂O₁₁
Molecular Weight:818.877
Hs Code.:

Synonyms:(2S,3R,4R,5R)-2,3,5-Tris(benzoyloxy)-3-(benzyloxy)-1,1-bis[(benzoyloxy)methyl]cyclohexane

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Chemical Property of (2S,3R,4R,5R)-2,3,5-Tris(benzoyloxy)-3-(benzyloxy)-1,1-bis[(benzoyloxy)methyl]cyclohexane

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Technology Process of (2S,3R,4R,5R)-2,3,5-Tris(benzoyloxy)-3-(benzyloxy)-1,1-bis[(benzoyloxy)methyl]cyclohexane

There total 5 articles about (2S,3R,4R,5R)-2,3,5-Tris(benzoyloxy)-3-(benzyloxy)-1,1-bis[(benzoyloxy)methyl]cyclohexane 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%

: 98-88-4
benzoyl chloride

: 360562-15-8
(1R,2R,3R,4S)-3-(Benzyloxy)-5,5-bis(hydroxymethyl)cyclohexane-1,2,4-triol

: 360562-16-9
(2S,3R,4R,5R)-2,3,5-Tris(benzoyloxy)-3-(benzyloxy)-1,1-bis[(benzoyloxy)methyl]cyclohexane

Guidance literature:: With pyridine; at 20 ℃; for 50h;
DOI:10.1135/cccc20010785

Reference yield:

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

: 360562-16-9
(2S,3R,4R,5R)-2,3,5-Tris(benzoyloxy)-3-(benzyloxy)-1,1-bis[(benzoyloxy)methyl]cyclohexane

Guidance literature:: Multi-step reaction with 4 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

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

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

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

Reference yield:

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

: 360562-16-9
(2S,3R,4R,5R)-2,3,5-Tris(benzoyloxy)-3-(benzyloxy)-1,1-bis[(benzoyloxy)methyl]cyclohexane

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: aq. NaIO₄ / dioxane

1.3: 35 percent / pyridine / 48 h / 20 °C

2.1: 79 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

3.1: 93 percent / pyridine / 50 h / 20 °C

With pyridine; lithium aluminium tetrahydride; Dowex 50(H(+)); water; In tetrahydrofuran; 1,4-dioxane;
DOI:10.1135/cccc20010785