(2R,3S)-3-((E)-(2R,7S)-9-Benzyloxy-2,6,7-trimethyl-4-methylene-non-5-enyl)-oxirane-2-carbaldehyde

Base Information

• Chemical Name: (2R,3S)-3-((E)-(2R,7S)-9-Benzyloxy-2,6,7-trimethyl-4-methylene-non-5-enyl)-oxirane-2-carbaldehyde
• CAS No.: 219654-07-6
• Molecular Formula: C₂₃H₃₂O₃
• Molecular Weight: 356.505
• Mol file: 219654-07-6.mol

Synonyms:

Chemical Property of (2R,3S)-3-((E)-(2R,7S)-9-Benzyloxy-2,6,7-trimethyl-4-methylene-non-5-enyl)-oxirane-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-((E)-(2R,7S)-9-Benzyloxy-2,6,7-trimethyl-4-methylene-non-5-enyl)-oxirane-2-carbaldehyde

There total 19 articles about (2R,3S)-3-((E)-(2R,7S)-9-Benzyloxy-2,6,7-trimethyl-4-methylene-non-5-enyl)-oxirane-2-carbaldehyde 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:

[(2R,3R)-3-((E)-(2R,7S)-9-Benzyloxy-2,6,7-trimethyl-4-methylene-non-5-enyl)-oxiranyl]-methanol (219654-16-7) → (2R,3S)-3-((E)-(2R,7S)-9-Benzyloxy-2,6,7-trimethyl-4-methylene-non-5-enyl)-oxirane-2-carbaldehyde (219654-07-6)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃; for 1.5h;

DOI:10.1016/S0040-4039(98)02009-7

Reference yield:

Methanesulfonic acid (S)-4-benzyloxy-2-methyl-butyl ester → (2R,3S)-3-((E)-(2R,7S)-9-Benzyloxy-2,6,7-trimethyl-4-methylene-non-5-enyl)-oxirane-2-carbaldehyde (219654-07-6)

Guidance literature:

Multi-step reaction with 14 steps

1: K₂CO₃ / dimethylformamide / 0.5 h / 25 °C

2: mCPBA / CH₂Cl₂ / 3 h / 0 - 25 °C

3: H₂ / Pd/C / methanol / 1 h / 25 °C

4: Et₃N, DMAP / CH₂Cl₂ / 3 h / 25 °C

5: n-BuLi / tetrahydrofuran / 1 h / -78 - 0 °C

6: o-iodoxybenzoic acid / dimethylsulfoxide / 1 h / 25 °C

7: 60 percent / lithium naphthalenide / tetrahydrofuran / 1 h / -78 °C

8: 88 percent / diethyl ether / 0.5 h / 0 °C

9: TBAF / tetrahydrofuran / 5 h / 25 °C

10: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

11: benzene / 1 h / 25 °C

12: DIBAL / CH₂Cl₂ / 1 h / -78 °C

13: Ti(i-PrO)4, (+)-diethyl L-tartrate, TBHP / CH₂Cl₂ / 12 h / -10 °C

14: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; naphthalen-1-yl-lithium; 3-chloro-benzenecarboperoxoic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(98)02009-7

Reference yield:

(2S)-4-(benzyloxy)-1-(phenylsulfonyl)-2-methylbutane (88408-99-5) → (2R,3S)-3-((E)-(2R,7S)-9-Benzyloxy-2,6,7-trimethyl-4-methylene-non-5-enyl)-oxirane-2-carbaldehyde (219654-07-6)

Guidance literature:

Multi-step reaction with 12 steps

1: H₂ / Pd/C / methanol / 1 h / 25 °C

2: Et₃N, DMAP / CH₂Cl₂ / 3 h / 25 °C

3: n-BuLi / tetrahydrofuran / 1 h / -78 - 0 °C

4: o-iodoxybenzoic acid / dimethylsulfoxide / 1 h / 25 °C

5: 60 percent / lithium naphthalenide / tetrahydrofuran / 1 h / -78 °C

6: 88 percent / diethyl ether / 0.5 h / 0 °C

7: TBAF / tetrahydrofuran / 5 h / 25 °C

8: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

9: benzene / 1 h / 25 °C

10: DIBAL / CH₂Cl₂ / 1 h / -78 °C

11: Ti(i-PrO)4, (+)-diethyl L-tartrate, TBHP / CH₂Cl₂ / 12 h / -10 °C

12: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; naphthalen-1-yl-lithium; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1016/S0040-4039(98)02009-7

upstream raw materials:

[(2R,3R)-3-((E)-(2R,7S)-9-Benzyloxy-2,6,7-trimethyl-4-methylene-non-5-enyl)-oxiranyl]-methanol

(3S)-3-methyl-4-phenylsulfonylbutanol

(2S)-2-methyl-4-(benzyloxy)-1-butanal

(2S)-4-(benzyloxy)-1-(phenylsulfonyl)-2-methylbutane