(2R,4R,5S)-(E)-4-diphenylmethoxyiminomethyl-5-[(z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane

Base Information

Chemical Name:(2R,4R,5S)-(E)-4-diphenylmethoxyiminomethyl-5-[(z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane
CAS No.:119252-57-2
Molecular Formula:C₂₇H₃₃NO₅
Molecular Weight:451.563
Hs Code.:

Synonyms:(2R,4R,5S)-(E)-4-diphenylmethoxyiminomethyl-5-[(z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane

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Chemical Property of (2R,4R,5S)-(E)-4-diphenylmethoxyiminomethyl-5-[(z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane

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Technology Process of (2R,4R,5S)-(E)-4-diphenylmethoxyiminomethyl-5-[(z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane

There total 13 articles about (2R,4R,5S)-(E)-4-diphenylmethoxyiminomethyl-5-[(z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane 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: 82.1%

: 776-74-9
Bromodiphenylmethane

: 119323-06-7
(2R,4R,5S)-(E)-4-hydroxyiminomethyl-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane

: 119252-57-2
(2R,4R,5S)-(E)-4-diphenylmethoxyiminomethyl-5-[(z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane

Guidance literature:: (2R,4R,5S)-(E)-4-hydroxyiminomethyl-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane; With sodium hydride; In N,N-dimethyl-formamide; at 5 ℃; for 0.5h;

Bromodiphenylmethane; at 0 ℃; for 2h;
DOI:10.1016/S0968-0896(99)00204-7

Reference yield:

: 70369-46-9,421549-37-3
(2R,4S,5R)-4-hydroxymethyl-2-methyl-1,3-dioxan-5-ol

: 119252-57-2
(2R,4R,5S)-(E)-4-diphenylmethoxyiminomethyl-5-[(z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 11 steps

1.1: 100 percent / imidazole / dimethylformamide / 2 h / 20 °C

2.1: 77.3 percent / DMSO; TFA; DCC / benzene; pyridine / 3 h / 20 °C

3.1: 65.9 percent / tetrahydrofuran / 24 h / 20 °C

4.1: 55.7 percent / H₂ / Pd/C / ethanol / 1.5 h / 20 °C / 760 Torr

5.1: 81 percent / DIBAL-H / toluene / 1 h / -78 °C

6.1: NaH / dimethylsulfoxide / 0.25 h / 20 °C

6.2: 67.7 percent / dimethylsulfoxide / 1.5 h / 30 °C

7.1: K₂CO₃ / dimethylformamide / 5 h / 20 °C

8.1: 100 percent / nBu₄NF / tetrahydrofuran / 3 h / 20 °C

9.1: 67.7 percent / CrO₃; pyridine / CH₂Cl₂ / 2 h

10.1: 41.3 percent / NH₂OH*HCl; NaHCO₃ / methanol; H₂O / 3 h / 20 °C

11.1: NaH / dimethylformamide / 0.5 h / 5 °C

11.2: 82.1 percent / 2 h / 0 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene; 1.1: Substitution / 2.1: Oxidation / 3.1: Wittig reaction / 4.1: Catalytic hydrogenation / 5.1: Reduction / 6.1: Elimination / 6.2: Wittig reaction / 7.1: Methylation / 8.1: desilylation / 9.1: Oxidation / 10.1: Condensation / 11.1: Metallation / 11.2: Substitution;
DOI:10.1016/S0968-0896(99)00204-7

Reference yield:

: 18465-50-4,13224-97-0,13224-98-1,13224-99-2,13225-00-8,13225-01-9,13225-02-0,87068-63-1
4,6-O-ethylidene-D-glucopyranose

: 119252-57-2
(2R,4R,5S)-(E)-4-diphenylmethoxyiminomethyl-5-[(z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 13 steps

1.1: NaIO₄ / H₂O / 5 °C

2.1: NaBH₄ / ethanol / 5 °C

3.1: 100 percent / imidazole / dimethylformamide / 2 h / 20 °C

4.1: 77.3 percent / DMSO; TFA; DCC / benzene; pyridine / 3 h / 20 °C

5.1: 65.9 percent / tetrahydrofuran / 24 h / 20 °C

6.1: 55.7 percent / H₂ / Pd/C / ethanol / 1.5 h / 20 °C / 760 Torr

7.1: 81 percent / DIBAL-H / toluene / 1 h / -78 °C

8.1: NaH / dimethylsulfoxide / 0.25 h / 20 °C

8.2: 67.7 percent / dimethylsulfoxide / 1.5 h / 30 °C

9.1: K₂CO₃ / dimethylformamide / 5 h / 20 °C

10.1: 100 percent / nBu₄NF / tetrahydrofuran / 3 h / 20 °C

11.1: 67.7 percent / CrO₃; pyridine / CH₂Cl₂ / 2 h

12.1: 41.3 percent / NH₂OH*HCl; NaHCO₃ / methanol; H₂O / 3 h / 20 °C

13.1: NaH / dimethylformamide / 0.5 h / 5 °C

13.2: 82.1 percent / 2 h / 0 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; sodium tetrahydroborate; sodium periodate; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene; 1.1: Oxidation / 2.1: Reduction / 3.1: Substitution / 4.1: Oxidation / 5.1: Wittig reaction / 6.1: Catalytic hydrogenation / 7.1: Reduction / 8.1: Elimination / 8.2: Wittig reaction / 9.1: Methylation / 10.1: desilylation / 11.1: Oxidation / 12.1: Condensation / 13.1: Metallation / 13.2: Substitution;
DOI:10.1016/S0968-0896(99)00204-7