N-[(2R,4aR,6S,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-4-hexadecyloxy-3-methoxy-butylsulfanyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Base Information

Chemical Name:N-[(2R,4aR,6S,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-4-hexadecyloxy-3-methoxy-butylsulfanyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide
CAS No.:324534-81-8
Molecular Formula:C₄₂H₇₅NO₇SSi
Molecular Weight:766.212
Hs Code.:

N-[(2R,4aR,6S,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-4-hexadecyloxy-3-methoxy-butylsulfanyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Synonyms:N-[(2R,4aR,6S,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-4-hexadecyloxy-3-methoxy-butylsulfanyl)-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,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-4-hexadecyloxy-3-methoxy-butylsulfanyl)-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,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-4-hexadecyloxy-3-methoxy-butylsulfanyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

There total 10 articles about N-[(2R,4aR,6S,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-4-hexadecyloxy-3-methoxy-butylsulfanyl)-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: 93.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 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

: 324534-81-8
N-[(2R,4aR,6S,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-4-hexadecyloxy-3-methoxy-butylsulfanyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 5h;
DOI:10.1021/ol006783a

Reference yield:

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

: 324534-81-8
N-[(2R,4aR,6S,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-4-hexadecyloxy-3-methoxy-butylsulfanyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Guidance literature:: Multi-step reaction with 9 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

9.1: 93 percent / imidazole / dimethylformamide / 5 h / 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

: 324534-81-8
N-[(2R,4aR,6S,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-4-hexadecyloxy-3-methoxy-butylsulfanyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Guidance literature:: Multi-step reaction with 4 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

4.1: 93 percent / imidazole / dimethylformamide / 5 h / 20 °C

With 1H-imidazole; hydrazinium monoacetate; toluene-4-sulfonic acid; guanidine nitrate; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol006783a