N-cyclohexyl (3S,4S,5R)-3-hydroxy-4,5-O-isopropylidene-1-cyclohexene-1-carboxamide

Base Information

Chemical Name:N-cyclohexyl (3S,4S,5R)-3-hydroxy-4,5-O-isopropylidene-1-cyclohexene-1-carboxamide
CAS No.:1053258-56-2
Molecular Formula:C₁₆H₂₅NO₄
Molecular Weight:295.379
Hs Code.:

Synonyms:N-cyclohexyl (3S,4S,5R)-3-hydroxy-4,5-O-isopropylidene-1-cyclohexene-1-carboxamide

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Chemical Property of N-cyclohexyl (3S,4S,5R)-3-hydroxy-4,5-O-isopropylidene-1-cyclohexene-1-carboxamide

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Technology Process of N-cyclohexyl (3S,4S,5R)-3-hydroxy-4,5-O-isopropylidene-1-cyclohexene-1-carboxamide

There total 5 articles about N-cyclohexyl (3S,4S,5R)-3-hydroxy-4,5-O-isopropylidene-1-cyclohexene-1-carboxamide 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: 77.0%

: 1026076-08-3
N-cyclohexyl (4R,5R)-4,5-O-isopropylidene-3-oxo-1-cyclohexene-1-carboxamide

: 1053258-56-2
N-cyclohexyl (3S,4S,5R)-3-hydroxy-4,5-O-isopropylidene-1-cyclohexene-1-carboxamide

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;
DOI:10.1016/j.carres.2003.10.026

Reference yield:

: 32384-42-2
(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

: 1053258-56-2
N-cyclohexyl (3S,4S,5R)-3-hydroxy-4,5-O-isopropylidene-1-cyclohexene-1-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / 0.33 h / microwave irradiation

2: 81 percent / pyridinium chlorochromate; 4A MS / CH₂Cl₂ / 3 h / 20 °C

3: 85 percent / phosphorus oxychloride / pyridine / 25 h / 20 °C

4: 77 percent / NaBH₄ / methanol / 0.33 h / 0 °C

With sodium tetrahydroborate; pyridinium chlorochromate; trichlorophosphate; In pyridine; methanol; dichloromethane;
DOI:10.1016/j.carres.2003.10.026

Reference yield:

: 77-95-2
D-(-)-quinic acid

: 1053258-56-2
N-cyclohexyl (3S,4S,5R)-3-hydroxy-4,5-O-isopropylidene-1-cyclohexene-1-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / Na₂SO₄; H₂SO₄ / 1 h / Heating

2: 97 percent / 0.33 h / microwave irradiation

3: 81 percent / pyridinium chlorochromate; 4A MS / CH₂Cl₂ / 3 h / 20 °C

4: 85 percent / phosphorus oxychloride / pyridine / 25 h / 20 °C

5: 77 percent / NaBH₄ / methanol / 0.33 h / 0 °C

With sodium tetrahydroborate; sulfuric acid; sodium sulfate; pyridinium chlorochromate; trichlorophosphate; In pyridine; methanol; dichloromethane;
DOI:10.1016/j.carres.2003.10.026