(2S,3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-N-methoxy-6-{[(4-methoxybenzyl)oxy]methyl}-N-methyl-2-propylnon-6-enamide

Base Information

• Chemical Name: (2S,3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-N-methoxy-6-{[(4-methoxybenzyl)oxy]methyl}-N-methyl-2-propylnon-6-enamide
• CAS No.: 912654-41-2
• Molecular Formula: C₂₉H₅₁NO₆Si
• Molecular Weight: 537.813

Synonyms:(2S,3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-N-methoxy-6-{[(4-methoxybenzyl)oxy]methyl}-N-methyl-2-propylnon-6-enamide

Chemical Property of (2S,3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-N-methoxy-6-{[(4-methoxybenzyl)oxy]methyl}-N-methyl-2-propylnon-6-enamide

Chemical Property:

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Technology Process of (2S,3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-N-methoxy-6-{[(4-methoxybenzyl)oxy]methyl}-N-methyl-2-propylnon-6-enamide

There total 11 articles about (2S,3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-N-methoxy-6-{[(4-methoxybenzyl)oxy]methyl}-N-methyl-2-propylnon-6-enamide 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: 66.0%

(S)-4-Benzyl-3-[(E)-(2S,3R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-propyl-non-6-enoyl]-oxazolidin-2-one (912654-40-1) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → (2S,3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-N-methoxy-6-{[(4-methoxybenzyl)oxy]methyl}-N-methyl-2-propylnon-6-enamide (912654-41-2)

Guidance literature:

With trimethylaluminum; In tetrahydrofuran; toluene; at 0 - 20 ℃; for 16h;

DOI:10.1021/jo061104g

Reference yield:

(2E)-2-{[(4-methoxybenzyl)oxy]methyl}pent-2-enal (912654-35-4) → (2S,3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-N-methoxy-6-{[(4-methoxybenzyl)oxy]methyl}-N-methyl-2-propylnon-6-enamide (912654-41-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: TiCl₄ / CH₂Cl₂ / 0.08 h / 0 °C

1.2: iPr₂NEt / CH₂Cl₂ / 2 h / -78 °C

1.3: 70 percent / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 23 °C

3.1: 84 percent / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

4.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3.5 h / -78 - 20 °C

5.1: Bu₂BOTf; triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

5.2: CH₂Cl₂ / 1.5 h / -78 - 20 °C

6.1: 66 percent / AlMe₃ / tetrahydrofuran; toluene / 16 h / 0 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; 5.2: Evans aldol reaction;

DOI:10.1021/jo061104g

Reference yield:

(2Z)-2-{[(4-methoxybenzyl)oxy]methyl}pent-2-en-1-ol (912654-34-3) → (2S,3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-N-methoxy-6-{[(4-methoxybenzyl)oxy]methyl}-N-methyl-2-propylnon-6-enamide (912654-41-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3.5 h / -78 - 20 °C

2.1: TiCl₄ / CH₂Cl₂ / 0.08 h / 0 °C

2.2: iPr₂NEt / CH₂Cl₂ / 2 h / -78 °C

2.3: 70 percent / CH₂Cl₂ / 0.5 h / -78 °C

3.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 23 °C

4.1: 84 percent / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

5.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3.5 h / -78 - 20 °C

6.1: Bu₂BOTf; triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

6.2: CH₂Cl₂ / 1.5 h / -78 - 20 °C

7.1: 66 percent / AlMe₃ / tetrahydrofuran; toluene / 16 h / 0 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; 6.2: Evans aldol reaction;

DOI:10.1021/jo061104g

upstream raw materials:

(S)-4-Benzyl-3-[(E)-(2S,3R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-propyl-non-6-enoyl]-oxazolidin-2-one

N,O-dimethylhydroxylamine*hydrochloride

(2E)-2-{[(4-methoxybenzyl)oxy]methyl}pent-2-enal

(2Z)-2-{[(4-methoxybenzyl)oxy]methyl}pent-2-en-1-ol

Downstream raw materials:

(R)-1-[3-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isobutyl-2,4-bis-methoxymethoxy-phenyl]-2-{(4R,6R)-6-[(E)-1-(4-methoxy-benzyloxymethyl)-but-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pentan-1-ol

(R)-1-(3-Hydroxymethyl-5-isobutyl-2,4-bis-methoxymethoxy-phenyl)-2-{(4R,6R)-6-[(E)-1-(4-methoxy-benzyloxymethyl)-but-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pentan-1-ol

3-isobutyl-5-{(2S)-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]pentanoyl}-2,6-bis(methoxymethoxy)benzaldehyde

3-((2S)-2-{(4R,6R)-6-[(1E)-1-(hydroxymethyl)but-1-enyl]-2,2-dimethyl-1,3-dioxan-4-yl}pentanoyl)-5-isobutyl-2,6-bis(methoxymethoxy)benzaldehyde

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