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

Base Information

Chemical Name:(3S,4R,5S)-3,4,5-tris(benzyloxy)-1-cyclohexenecarbaldehyde
CAS No.:115184-62-8
Molecular Formula:C₂₈H₂₈O₄
Molecular Weight:428.528
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-cyclohexenecarbaldehyde

Chemical Property:

Purity/Quality:

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

There total 10 articles about (3S,4R,5S)-3,4,5-tris(benzyloxy)-1-cyclohexenecarbaldehyde 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:

: 115184-59-3
(1R,2S,3S,4R,5S)-3,4,5-tris(benzyloxy)-2-hydroxycyclohexanecarbaldehyde

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

Guidance literature:: With methanesulfonyl chloride; In pyridine; for 14h; Ambient temperature;
DOI:10.1246/bcsj.60.2189

Reference yield:

: 100-39-0
benzyl bromide

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

Guidance literature:: Multi-step reaction with 5 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

With sodium tetrahydroborate; sodium periodate; sodium hydride; acetic acid; methanesulfonyl chloride; In 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

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

Guidance literature:: Multi-step reaction with 9 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

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