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

Base Information

• Chemical Name: 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
• CAS No.: 410077-72-4
• Molecular Formula: C₄₅H₆₄O₈Si
• Molecular Weight: 761.084
• Mol file: 410077-72-4.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 23 articles about 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 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: 100.0%

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 (410077-71-3) + triethylsilyl trifluoromethyl sulfonate (79271-56-0) → 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 (410077-72-4)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 - 0 ℃;

DOI:10.1021/ol017273z

Reference yield:

3-(naphthalen-2-ylmethoxy)-propan-1-ol (410077-63-3) → 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 (410077-72-4)

Guidance literature:

Multi-step reaction with 10 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

8.1: Hg(ClO₄)2*4H₂O / acetonitrile; H₂O; CH₂Cl₂ / 0.17 h / 0 °C

8.2: 83 percent / HClO₄ / acetonitrile; H₂O; CH₂Cl₂ / 0.08 h

9.1: 90 percent / pyridine; 4-DMAP / CH₂Cl₂ / 13 h

10.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; mercury(II) perchlorate; [(+)-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; water; sodium hydrogencarbonate; toluene; acetonitrile; pentane;

DOI:10.1021/ol017273z

Reference yield:

2-bromomethylnaphthyl bromide (939-26-4) → 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 (410077-72-4)

Guidance literature:

Multi-step reaction with 11 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

9.1: Hg(ClO₄)2*4H₂O / acetonitrile; H₂O; CH₂Cl₂ / 0.17 h / 0 °C

9.2: 83 percent / HClO₄ / acetonitrile; H₂O; CH₂Cl₂ / 0.08 h

10.1: 90 percent / pyridine; 4-DMAP / CH₂Cl₂ / 13 h

11.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; mercury(II) perchlorate; [(+)-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; water; sodium hydrogencarbonate; toluene; acetonitrile; pentane;

DOI:10.1021/ol017273z

upstream 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

triethylsilyl trifluoromethyl sulfonate

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)-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

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

{(2R,4S,6S,8S,10S)-4-Acetoxy-8-[(R)-4-(4-methoxy-benzyloxy)-3-methyl-2-methylene-butyl]-10-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl}-acetic acid

C₄₃H₇₄O₉Si₂