(1R,2R,3S)-1-benzoyloxymethyl-1,2-O,O-isopropylidene-3-hydroxy-cyclohex-4-ene

Base Information

Chemical Name:(1R,2R,3S)-1-benzoyloxymethyl-1,2-O,O-isopropylidene-3-hydroxy-cyclohex-4-ene
CAS No.:696574-77-3
Molecular Formula:C₁₇H₂₀O₅
Molecular Weight:304.343
Hs Code.:

Synonyms:(1R,2R,3S)-1-benzoyloxymethyl-1,2-O,O-isopropylidene-3-hydroxy-cyclohex-4-ene

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Chemical Property of (1R,2R,3S)-1-benzoyloxymethyl-1,2-O,O-isopropylidene-3-hydroxy-cyclohex-4-ene

Chemical Property:

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Technology Process of (1R,2R,3S)-1-benzoyloxymethyl-1,2-O,O-isopropylidene-3-hydroxy-cyclohex-4-ene

There total 9 articles about (1R,2R,3S)-1-benzoyloxymethyl-1,2-O,O-isopropylidene-3-hydroxy-cyclohex-4-ene 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: 94.0%

: 696574-69-3
(1R,2R,3S)-1-benzoyloxymethyl-1,2-O,O-isopropylidene-3-O-(tert-butyldimethylsilyl)-cyclohex-4-ene

: 696574-77-3
(1R,2R,3S)-1-benzoyloxymethyl-1,2-O,O-isopropylidene-3-hydroxy-cyclohex-4-ene

Guidance literature:: With tetrabutyl ammonium fluoride; benzoic acid; In tetrahydrofuran; at 20 ℃; for 24h;
DOI:10.1016/j.tet.2004.02.066

Reference yield:

: 138-59-0
shikimic acid

: 696574-77-3
(1R,2R,3S)-1-benzoyloxymethyl-1,2-O,O-isopropylidene-3-hydroxy-cyclohex-4-ene

Guidance literature:: Multi-step reaction with 10 steps

1: 93 percent / SOCl₂ / 0 - 20 °C

2: 87 percent / (+/-)-camphorsulfonic acid / methanol / 48 h / 90 °C

3: 97 percent / imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

4: 92 percent / diisobutylaluminium hydride / toluene / 0.33 h / -78 °C / d

5: 97 percent / 4-(dimethylamino)pyridine; pyridine / 2.33 h / 20 °C

6: 94 percent / N-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; H₂O / 12 h / 20 °C

7: 99 percent / p-toluenesulfonic acid / CH₂Cl₂ / 3 h / 20 °C

8: 80 percent / trifluoroacetic acid / H₂O; CH₂Cl₂ / 6 h

9: 87 percent / imidazole; triphenylphosphine; iodine / toluene / 4 h / Heating

10: 94 percent / tetrabutylammonium fluoride; benzoic acid / tetrahydrofuran / 24 h / 20 °C

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; thionyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; iodine; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triphenylphosphine; benzoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1016/j.tet.2004.02.066

Reference yield:

: 40983-58-2
methyl shikimate

: 696574-77-3
(1R,2R,3S)-1-benzoyloxymethyl-1,2-O,O-isopropylidene-3-hydroxy-cyclohex-4-ene

Guidance literature:: Multi-step reaction with 9 steps

1: 87 percent / (+/-)-camphorsulfonic acid / methanol / 48 h / 90 °C

2: 97 percent / imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

3: 92 percent / diisobutylaluminium hydride / toluene / 0.33 h / -78 °C / d

4: 97 percent / 4-(dimethylamino)pyridine; pyridine / 2.33 h / 20 °C

5: 94 percent / N-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; H₂O / 12 h / 20 °C

6: 99 percent / p-toluenesulfonic acid / CH₂Cl₂ / 3 h / 20 °C

7: 80 percent / trifluoroacetic acid / H₂O; CH₂Cl₂ / 6 h

8: 87 percent / imidazole; triphenylphosphine; iodine / toluene / 4 h / Heating

9: 94 percent / tetrabutylammonium fluoride; benzoic acid / tetrahydrofuran / 24 h / 20 °C

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; iodine; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triphenylphosphine; benzoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1016/j.tet.2004.02.066