N-[(2R,4aR,6S,7R,8R,8aS)-6-((S)-4-Hexadecyloxy-3-methoxy-butylsulfanyl)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Base Information

Chemical Name:N-[(2R,4aR,6S,7R,8R,8aS)-6-((S)-4-Hexadecyloxy-3-methoxy-butylsulfanyl)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide
CAS No.:324534-43-2
Molecular Formula:C₃₆H₆₁NO₇S
Molecular Weight:651.949
Hs Code.:

Synonyms:N-[(2R,4aR,6S,7R,8R,8aS)-6-((S)-4-Hexadecyloxy-3-methoxy-butylsulfanyl)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

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Chemical Property of N-[(2R,4aR,6S,7R,8R,8aS)-6-((S)-4-Hexadecyloxy-3-methoxy-butylsulfanyl)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

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Technology Process of N-[(2R,4aR,6S,7R,8R,8aS)-6-((S)-4-Hexadecyloxy-3-methoxy-butylsulfanyl)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

There total 9 articles about N-[(2R,4aR,6S,7R,8R,8aS)-6-((S)-4-Hexadecyloxy-3-methoxy-butylsulfanyl)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 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: 90.0%

: 1125-88-8
benzaldehyde dimethyl acetal

: 324534-75-0
N-[(2S,3R,4R,5S,6R)-2-((S)-4-Hexadecyloxy-3-methoxy-butylsulfanyl)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide

: 324534-43-2
N-[(2R,4aR,6S,7R,8R,8aS)-6-((S)-4-Hexadecyloxy-3-methoxy-butylsulfanyl)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Guidance literature:: With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/ol006783a

Reference yield:

: 324534-26-1
(R)-2-phenyl-(S)-4-hexadecyloxymethyl-1,3-dioxane

: 324534-43-2
N-[(2R,4aR,6S,7R,8R,8aS)-6-((S)-4-Hexadecyloxy-3-methoxy-butylsulfanyl)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: 82 percent / 80percent AcOH / 1 h / 90 °C

2.1: 97 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

3.1: 92 percent / NaH; Bu₄NI / tetrahydrofuran / 4 h

4.1: 0.748 g / Bu₄NF / tetrahydrofuran / 2 h / 20 °C

5.1: 75 percent / PPh₃; I₂; imidazole / toluene / 1 h / 120 °C

6.1: NH₂NH₂*HOAc / dimethylformamide / 1 h / 20 °C

6.2: 87 percent / Et₃N / dimethylformamide / 5 h

7.1: 0.13 g / guanidine / ethanol; CH₂Cl₂ / 0.33 h / 20 °C

8.1: 90 percent / p-TsOH / dimethylformamide / 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; iodine; hydrazinium monoacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; guanidine nitrate; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol006783a

Reference yield:

: 10043-46-6,129693-99-8,129694-00-4
2-acetamido-3,4,6-tri-O-acetyl-1-S-acetyl-2-deoxy-1-thio-β-D-glucopyranoside

: 324534-43-2
N-[(2R,4aR,6S,7R,8R,8aS)-6-((S)-4-Hexadecyloxy-3-methoxy-butylsulfanyl)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: NH₂NH₂*HOAc / dimethylformamide / 1 h / 20 °C

1.2: 87 percent / Et₃N / dimethylformamide / 5 h

2.1: 0.13 g / guanidine / ethanol; CH₂Cl₂ / 0.33 h / 20 °C

3.1: 90 percent / p-TsOH / dimethylformamide / 20 °C

With hydrazinium monoacetate; toluene-4-sulfonic acid; guanidine nitrate; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol006783a