(2S,4S,7R)-8-(4-Methoxy-benzyloxy)-2,7-dimethyl-6-methylene-1-{2-[(2S,4S)-6-(naphthalen-2-ylmethoxy)-2,4-bis-triethylsilanyloxy-hexyl]-[1,3]dithian-2-yl}-octane-2,4-diol

Base Information

• Chemical Name: (2S,4S,7R)-8-(4-Methoxy-benzyloxy)-2,7-dimethyl-6-methylene-1-{2-[(2S,4S)-6-(naphthalen-2-ylmethoxy)-2,4-bis-triethylsilanyloxy-hexyl]-[1,3]dithian-2-yl}-octane-2,4-diol
• CAS No.: 410077-49-5
• Molecular Formula: C₅₂H₈₄O₇S₂Si₂
• Molecular Weight: 941.538

Synonyms:(2S,4S,7R)-8-(4-Methoxy-benzyloxy)-2,7-dimethyl-6-methylene-1-{2-[(2S,4S)-6-(naphthalen-2-ylmethoxy)-2,4-bis-triethylsilanyloxy-hexyl]-[1,3]dithian-2-yl}-octane-2,4-diol

Chemical Property of (2S,4S,7R)-8-(4-Methoxy-benzyloxy)-2,7-dimethyl-6-methylene-1-{2-[(2S,4S)-6-(naphthalen-2-ylmethoxy)-2,4-bis-triethylsilanyloxy-hexyl]-[1,3]dithian-2-yl}-octane-2,4-diol

Chemical Property:

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Technology Process of (2S,4S,7R)-8-(4-Methoxy-benzyloxy)-2,7-dimethyl-6-methylene-1-{2-[(2S,4S)-6-(naphthalen-2-ylmethoxy)-2,4-bis-triethylsilanyloxy-hexyl]-[1,3]dithian-2-yl}-octane-2,4-diol

There total 19 articles about (2S,4S,7R)-8-(4-Methoxy-benzyloxy)-2,7-dimethyl-6-methylene-1-{2-[(2S,4S)-6-(naphthalen-2-ylmethoxy)-2,4-bis-triethylsilanyloxy-hexyl]-[1,3]dithian-2-yl}-octane-2,4-diol 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: 58.0%

(1,3-dithian-2-yl)triethylsilane + (2S,5R)-6-(4-Methoxy-benzyloxy)-5-methyl-4-methylene-1-((S)-2-methyl-oxiranyl)-hexan-2-ol (410077-46-2) + Triethyl-[(S)-3-(naphthalen-2-ylmethoxy)-1-(S)-1-oxiranylmethyl-propoxy]-silane (410077-28-0) → (2S,4S,7R)-8-(4-Methoxy-benzyloxy)-2,7-dimethyl-6-methylene-1-{2-[(2S,4S)-6-(naphthalen-2-ylmethoxy)-2,4-bis-triethylsilanyloxy-hexyl]-[1,3]dithian-2-yl}-octane-2,4-diol (410077-49-5)

Guidance literature:

(1,3-dithian-2-yl)triethylsilane; With tert.-butyl lithium; In diethyl ether; pentane; at -78 - -45 ℃; for 0.833333h;

Triethyl-[(S)-3-(naphthalen-2-ylmethoxy)-1-(S)-1-oxiranylmethyl-propoxy]-silane; In diethyl ether; pentane; at -45 - -20 ℃; for 4h;

(2S,5R)-6-(4-Methoxy-benzyloxy)-5-methyl-4-methylene-1-((S)-2-methyl-oxiranyl)-hexan-2-ol; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; diethyl ether; hexane; at -20 ℃; for 15h; Further stages.;

DOI:10.1021/ol017273z

Reference yield:

3-(naphthalen-2-ylmethoxy)-propan-1-ol (410077-63-3) → (2S,4S,7R)-8-(4-Methoxy-benzyloxy)-2,7-dimethyl-6-methylene-1-{2-[(2S,4S)-6-(naphthalen-2-ylmethoxy)-2,4-bis-triethylsilanyloxy-hexyl]-[1,3]dithian-2-yl}-octane-2,4-diol (410077-49-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / benzyltriethylammonium chloride; TEMPO; KBr / NaOCl / CH₂Cl₂; aq. NaHCO₃; various solvent(s) / 2 h / 0 °C

2.1: [(+)-Ipc]2BOMe / diethyl ether / 1 h / 20 °C

2.2: diethyl ether / 4.5 h / -78 °C

2.3: NaOH; H₂O₂ / H₂O; diethyl ether / 1 h / Heating

3.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

3.2: tetrahydrofuran / 0.25 h / 20 °C

4.1: 92.8 g / IBr / toluene; CH₂Cl₂ / 1.5 h / -78 °C

5.1: 83 percent / K₂CO₃ / methanol / 2 h

6.1: 90 percent / imidazole / tetrahydrofuran / 1 h

7.1: t-BuLi / diethyl ether; pentane / 0.83 h / -78 - -45 °C

7.2: diethyl ether; pentane / 4 h / -45 - -20 °C

7.3: 58 percent / HMPA; n-BuLi / hexane; diethyl ether; tetrahydrofuran / 15 h / -20 °C

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [(+)-Ipc]2BOMe; N-benzyl-N,N,N-triethylammonium chloride; tert.-butyl lithium; sodium hexamethyldisilazane; iodine(I) bromide; potassium carbonate; potassium bromide; sodium hypochlorite; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; sodium hydrogencarbonate; toluene; pentane;

DOI:10.1021/ol017273z

Reference yield:

2-bromomethylnaphthyl bromide (939-26-4) → (2S,4S,7R)-8-(4-Methoxy-benzyloxy)-2,7-dimethyl-6-methylene-1-{2-[(2S,4S)-6-(naphthalen-2-ylmethoxy)-2,4-bis-triethylsilanyloxy-hexyl]-[1,3]dithian-2-yl}-octane-2,4-diol (410077-49-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: KH / tetrahydrofuran / 0.33 h / 20 °C

1.2: 97 percent / tetrabutylammonium iodide / tetrahydrofuran / 16 h / 20 °C

2.1: 90 percent / benzyltriethylammonium chloride; TEMPO; KBr / NaOCl / CH₂Cl₂; aq. NaHCO₃; various solvent(s) / 2 h / 0 °C

3.1: [(+)-Ipc]2BOMe / diethyl ether / 1 h / 20 °C

3.2: diethyl ether / 4.5 h / -78 °C

3.3: NaOH; H₂O₂ / H₂O; diethyl ether / 1 h / Heating

4.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

4.2: tetrahydrofuran / 0.25 h / 20 °C

5.1: 92.8 g / IBr / toluene; CH₂Cl₂ / 1.5 h / -78 °C

6.1: 83 percent / K₂CO₃ / methanol / 2 h

7.1: 90 percent / imidazole / tetrahydrofuran / 1 h

8.1: t-BuLi / diethyl ether; pentane / 0.83 h / -78 - -45 °C

8.2: diethyl ether; pentane / 4 h / -45 - -20 °C

8.3: 58 percent / HMPA; n-BuLi / hexane; diethyl ether; tetrahydrofuran / 15 h / -20 °C

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [(+)-Ipc]2BOMe; N-benzyl-N,N,N-triethylammonium chloride; tert.-butyl lithium; sodium hexamethyldisilazane; iodine(I) bromide; potassium hydride; potassium carbonate; potassium bromide; sodium hypochlorite; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; sodium hydrogencarbonate; toluene; pentane;

DOI:10.1021/ol017273z

upstream raw materials:

(2S,5R)-6-(4-Methoxy-benzyloxy)-5-methyl-4-methylene-1-((S)-2-methyl-oxiranyl)-hexan-2-ol

Triethyl-[(S)-3-(naphthalen-2-ylmethoxy)-1-(S)-1-oxiranylmethyl-propoxy]-silane

3-(naphthalen-2-ylmethoxy)-propan-1-ol

(R)-1-(Naphthalen-2-ylmethoxy)-hex-5-en-3-ol

Downstream raw materials:

Acetic acid (2S,4S,6R,8S,10S)-10-hydroxy-8-[(R)-4-(4-methoxy-benzyloxy)-3-methyl-2-methylene-butyl]-10-methyl-2-[2-(naphthalen-2-ylmethoxy)-ethyl]-1,7-dioxa-spiro[5.5]undec-4-yl ester

Acetic acid (2S,4S,6R,8S,10S)-8-[(R)-4-(4-methoxy-benzyloxy)-3-methyl-2-methylene-butyl]-10-methyl-2-[2-(naphthalen-2-ylmethoxy)-ethyl]-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

Acetic acid (2R,4S,6S,8S,10S)-8-[(R)-4-(4-methoxy-benzyloxy)-3-methyl-2-methylene-butyl]-10-methyl-2-(2-oxo-ethyl)-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

Acetic acid (2S,4S,6R,8S,10S)-2-(2-hydroxy-ethyl)-8-[(R)-4-(4-methoxy-benzyloxy)-3-methyl-2-methylene-butyl]-10-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

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