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

Base Information

Chemical Name:(1R,2R,3R,4S)-3-(Benzyloxy)-5,5-bis(hydroxymethyl)cyclohexane-1,2,4-triol
CAS No.:360562-15-8
Molecular Formula:C₁₅H₂₂O₆
Molecular Weight:298.336
Hs Code.:

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

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Chemical Property of (1R,2R,3R,4S)-3-(Benzyloxy)-5,5-bis(hydroxymethyl)cyclohexane-1,2,4-triol

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Technology Process of (1R,2R,3R,4S)-3-(Benzyloxy)-5,5-bis(hydroxymethyl)cyclohexane-1,2,4-triol

There total 4 articles about (1R,2R,3R,4S)-3-(Benzyloxy)-5,5-bis(hydroxymethyl)cyclohexane-1,2,4-triol 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: 79.0%

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

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

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h; Heating;
DOI:10.1135/cccc20010785

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

With 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

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

Guidance literature:: Multi-step reaction with 2 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

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