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

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Chemical Name:N-{(2R,4aR,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-4-hexadecyloxy-3-methoxy-but-(Z)-ylidene]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide
CAS No.:324534-51-2
Molecular Formula:C₄₂H₇₃NO₇Si
Molecular Weight:732.13
Hs Code.:

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

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

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Chemical Property of N-{(2R,4aR,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-4-hexadecyloxy-3-methoxy-but-(Z)-ylidene]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

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Technology Process of N-{(2R,4aR,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-4-hexadecyloxy-3-methoxy-but-(Z)-ylidene]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

There total 12 articles about N-{(2R,4aR,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-4-hexadecyloxy-3-methoxy-but-(Z)-ylidene]-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: 70.0%

: 324534-46-5
N-[(2R,4aR,6S,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-4-hexadecyloxy-3-methoxy-butane-1-sulfonyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

: 324534-51-2
N-{(2R,4aR,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-4-hexadecyloxy-3-methoxy-but-(Z)-ylidene]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Guidance literature:: With aluminum oxide; potassium hydroxide; 1,2-dibromo-1,1,2,2-tetrafluoroethane; In tert-butyl alcohol; at 47 ℃;
DOI:10.1021/ol006783a

Reference yield:

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

: 324534-51-2
N-{(2R,4aR,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-4-hexadecyloxy-3-methoxy-but-(Z)-ylidene]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Guidance literature:: Multi-step reaction with 11 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

10.1: 95 percent / MMPP / H₂O; ethanol; tetrahydrofuran / 1 h / 55 °C

11.1: 70 percent / CF₂BrCF₂Br; KOH; Al₂O₃ / 2-methyl-propan-2-ol / 47 °C

With 1H-imidazole; aluminum oxide; potassium hydroxide; 1,2-dibromo-1,1,2,2-tetrafluoroethane; tetrabutyl ammonium fluoride; iodine; hydrazinium monoacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; guanidine nitrate; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 11.1: Ramberg-Baecklund rearrangement;
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

: 324534-51-2
N-{(2R,4aR,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-4-hexadecyloxy-3-methoxy-but-(Z)-ylidene]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Guidance literature:: Multi-step reaction with 6 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

5.1: 95 percent / MMPP / H₂O; ethanol; tetrahydrofuran / 1 h / 55 °C

6.1: 70 percent / CF₂BrCF₂Br; KOH; Al₂O₃ / 2-methyl-propan-2-ol / 47 °C

With 1H-imidazole; aluminum oxide; potassium hydroxide; 1,2-dibromo-1,1,2,2-tetrafluoroethane; hydrazinium monoacetate; toluene-4-sulfonic acid; guanidine nitrate; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 6.1: Ramberg-Baecklund rearrangement;
DOI:10.1021/ol006783a