[(2R,3R)-3-((1R,2R,3S,4R,5R,6S,7S)-8-Benzyloxy-1,3,5,7-tetramethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol

Base Information

• Chemical Name: [(2R,3R)-3-((1R,2R,3S,4R,5R,6S,7S)-8-Benzyloxy-1,3,5,7-tetramethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol
• CAS No.: 155430-52-7
• Molecular Formula: C₄₀H₇₈O₆Si₃
• Molecular Weight: 739.312
• Mol file: 155430-52-7.mol

Synonyms:[(2R,3R)-3-((1R,2R,3S,4R,5R,6S,7S)-8-Benzyloxy-1,3,5,7-tetramethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol

Chemical Property of [(2R,3R)-3-((1R,2R,3S,4R,5R,6S,7S)-8-Benzyloxy-1,3,5,7-tetramethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3R)-3-((1R,2R,3S,4R,5R,6S,7S)-8-Benzyloxy-1,3,5,7-tetramethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol

There total 23 articles about [(2R,3R)-3-((1R,2R,3S,4R,5R,6S,7S)-8-Benzyloxy-1,3,5,7-tetramethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol 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: 85.0%

(E)-(4R,5R,6S,7S,8R,9S,10S)-11-Benzyloxy-4,6,8,10-tetramethyl-5,7,9-tris-triethylsilanyloxy-undec-2-en-1-ol → [(2R,3R)-3-((1R,2R,3S,4R,5R,6S,7S)-8-Benzyloxy-1,3,5,7-tetramethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol (155430-52-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(98)00804-1

Reference yield:

(2R,3S,4S)-5-benzyloxy-2,3-epoxy-4-methyl-1-pentanol (73814-75-2,73814-80-9,73837-43-1,79027-31-9,81520-04-9,81520-05-0,81520-09-4,104320-78-7,115458-81-6,115458-82-7,125873-79-2,125873-80-5,81520-08-3) → [(2R,3R)-3-((1R,2R,3S,4R,5R,6S,7S)-8-Benzyloxy-1,3,5,7-tetramethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol (155430-52-7)

Guidance literature:

Multi-step reaction with 20 steps

1: (COCl)2, DMSO / CH₂Cl₂ / -70 °C

2: 1.) NaH / tetrahydrofuran / 1.) 0 deg C; 2.) -78 deg C

3: 95 percent / water / 1,2-dichloro-ethane / -30 °C

4: ImH, DMAP / dimethylformamide / 40 °C

5: 99 percent / DIBAH / toluene / -78 °C

6: MCPBA / CH₂Cl₂ / 0 °C

7: (COCl)2, DMSO / CH₂Cl₂ / -70 °C

8: 1.) NaH / tetrahydrofuran / 1.) 0 deg C; 2.) -78 deg C

9: 90 percent / Bu₄NF / tetrahydrofuran / 0 °C

10: 90 percent / water / 1,2-dichloro-ethane / -30 °C

11: ImH, DMAP / dimethylformamide / 40 °C

12: 99 percent / DIBAH / toluene / -78 °C

13: 79 percent / MCPBA / CH₂Cl₂ / 0 °C

14: (COCl)2, DMSO / CH₂Cl₂ / -70 °C

15: 1.) NaH / tetrahydrofuran / 1.) 0 deg C; 2.) -78 deg C

16: 96 percent / Bu₄NF / tetrahydrofuran / 0 °C

17: water / 1,2-dichloro-ethane / -30 °C

18: ImH, DMAP / dimethylformamide / 40 °C

19: 99 percent / DIBAH / toluene / -78 °C

20: MCPBA / CH₂Cl₂ / 0 °C

With 1H-imidazole; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)73733-6

Reference yield:

(R)-3-(benzyloxy)-2-methylpropan-1-ol (63930-49-4) → [(2R,3R)-3-((1R,2R,3S,4R,5R,6S,7S)-8-Benzyloxy-1,3,5,7-tetramethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol (155430-52-7)

Guidance literature:

Multi-step reaction with 24 steps

1: (COCl)2, DMSO / CH₂Cl₂ / -70 °C

2: 1.) potassium hydride, 18-crown-6 / tetrahydrofuran / 1.) 0 deg C; 2.) -78 deg C

3: 99 percent / DIBAH / toluene / -78 °C

4: 95 percent / MCPBA / CH₂Cl₂ / 0 °C

5: (COCl)2, DMSO / CH₂Cl₂ / -70 °C

6: 1.) NaH / tetrahydrofuran / 1.) 0 deg C; 2.) -78 deg C

7: 95 percent / water / 1,2-dichloro-ethane / -30 °C

8: ImH, DMAP / dimethylformamide / 40 °C

9: 99 percent / DIBAH / toluene / -78 °C

10: MCPBA / CH₂Cl₂ / 0 °C

11: (COCl)2, DMSO / CH₂Cl₂ / -70 °C

12: 1.) NaH / tetrahydrofuran / 1.) 0 deg C; 2.) -78 deg C

13: 90 percent / Bu₄NF / tetrahydrofuran / 0 °C

14: 90 percent / water / 1,2-dichloro-ethane / -30 °C

15: ImH, DMAP / dimethylformamide / 40 °C

16: 99 percent / DIBAH / toluene / -78 °C

17: 79 percent / MCPBA / CH₂Cl₂ / 0 °C

18: (COCl)2, DMSO / CH₂Cl₂ / -70 °C

19: 1.) NaH / tetrahydrofuran / 1.) 0 deg C; 2.) -78 deg C

20: 96 percent / Bu₄NF / tetrahydrofuran / 0 °C

21: water / 1,2-dichloro-ethane / -30 °C

22: ImH, DMAP / dimethylformamide / 40 °C

23: 99 percent / DIBAH / toluene / -78 °C

24: MCPBA / CH₂Cl₂ / 0 °C

With 1H-imidazole; dmap; oxalyl dichloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; water; potassium hydride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)73733-6

upstream raw materials:

(2R,3S,4S)-5-benzyloxy-2,3-epoxy-4-methyl-1-pentanol

(R)-3-(benzyloxy)-2-methylpropan-1-ol

(2S)-3-(benzyloxy)-2-methylpropanal

(Z)-(R)-5-Benzyloxy-4-methyl-pent-2-en-1-ol

Downstream raw materials:

2,2-Dimethyl-propionic acid (3S,4R,5R,6S,7R,8R,9S,10S)-11-benzyloxy-3-hydroxy-4,6,8,10-tetramethyl-5,7,9-tris-triethylsilanyloxy-undecyl ester

(3S,4R,5R,6S,7R,8R,9S,10S)-11-Benzyloxy-4,6,8,10-tetramethyl-5,7,9-tris-triethylsilanyloxy-undecane-1,3-diol