(3S,4R,5S)-3,4,5-tris(benzyloxy)-1-cyclohexene-1-methanol

Base Information

Chemical Name:(3S,4R,5S)-3,4,5-tris(benzyloxy)-1-cyclohexene-1-methanol
CAS No.:115224-12-9
Molecular Formula:C₂₈H₃₀O₄
Molecular Weight:430.544
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4R,5S)-3,4,5-tris(benzyloxy)-1-cyclohexene-1-methanol

Chemical Property:

Purity/Quality:

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Technology Process of (3S,4R,5S)-3,4,5-tris(benzyloxy)-1-cyclohexene-1-methanol

There total 11 articles about (3S,4R,5S)-3,4,5-tris(benzyloxy)-1-cyclohexene-1-methanol 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:

: 115184-62-8
(3S,4R,5S)-3,4,5-tris(benzyloxy)-1-cyclohexenecarbaldehyde

: 115224-12-9
(3S,4R,5S)-3,4,5-tris(benzyloxy)-1-cyclohexene-1-methanol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 4h;
DOI:10.1246/bcsj.60.2189

Reference yield:

: 100-39-0
benzyl bromide

: 115224-12-9
(3S,4R,5S)-3,4,5-tris(benzyloxy)-1-cyclohexene-1-methanol

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / sodium hydride / dimethylformamide / 12 h / Ambient temperature

2: acetic acid / H₂O; dioxane / 0.5 h / Heating

3: 84 mg / sodium borohydride / ethanol / 19 h / Ambient temperature

4: sodium periodate / methanol; H₂O / 2 h / 0 °C

5: methanesulfonyl chloride / pyridine / 14 h / Ambient temperature

6: 81 mg / lithium aluminium hydride / tetrahydrofuran / 4 h / 0 °C

With sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; sodium hydride; acetic acid; methanesulfonyl chloride; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.60.2189

Reference yield:

: 102561-99-9
(1R,2R,7R,9R)-11,11-dimethyl-8,10,12-trioxatricyclo<7.3.0.0^2,7>dodec-5-en-4-one

: 115224-12-9
(3S,4R,5S)-3,4,5-tris(benzyloxy)-1-cyclohexene-1-methanol

Guidance literature:: Multi-step reaction with 10 steps

1: 69 percent / diisobutylaluminium hydride / CH₂Cl₂; toluene / 1 h / -78 °C

2: 96 percent / pyridine / 4 h / Ambient temperature

3: 53 percent / osmium tetraoxide, hydrogen peroxide / 2-methyl-propan-2-ol; H₂O / 38 h / Ambient temperature

4: sodium methoxide / methanol / 0.5 h / 0 °C

5: 88 percent / sodium hydride / dimethylformamide / 12 h / Ambient temperature

6: acetic acid / H₂O; dioxane / 0.5 h / Heating

7: 84 mg / sodium borohydride / ethanol / 19 h / Ambient temperature

8: sodium periodate / methanol; H₂O / 2 h / 0 °C

9: methanesulfonyl chloride / pyridine / 14 h / Ambient temperature

10: 81 mg / lithium aluminium hydride / tetrahydrofuran / 4 h / 0 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; dihydrogen peroxide; sodium methylate; sodium hydride; diisobutylaluminium hydride; acetic acid; methanesulfonyl chloride; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1246/bcsj.60.2189