(3S,6R,7S,12S)-12-(benzyloxymethyl)-6-(2-mehtoxyethoxy)-3,7-dimethyloxacyclododec-10-en-2-one

Base Information

• Chemical Name: (3S,6R,7S,12S)-12-(benzyloxymethyl)-6-(2-mehtoxyethoxy)-3,7-dimethyloxacyclododec-10-en-2-one
• CAS No.: 1408299-20-6
• Molecular Formula: C₂₅H₃₈O₆
• Molecular Weight: 434.573
• Mol file: 1408299-20-6.mol

Synonyms:(3S,6R,7S,12S)-12-(benzyloxymethyl)-6-(2-mehtoxyethoxy)-3,7-dimethyloxacyclododec-10-en-2-one

Chemical Property of (3S,6R,7S,12S)-12-(benzyloxymethyl)-6-(2-mehtoxyethoxy)-3,7-dimethyloxacyclododec-10-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,6R,7S,12S)-12-(benzyloxymethyl)-6-(2-mehtoxyethoxy)-3,7-dimethyloxacyclododec-10-en-2-one

There total 15 articles about (3S,6R,7S,12S)-12-(benzyloxymethyl)-6-(2-mehtoxyethoxy)-3,7-dimethyloxacyclododec-10-en-2-one 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:

(2S,5R,6S)-((S)-1-(benzyloxy)but-3-en-2-yl) 5-((2-methoxyethoxy)methoxy)-2,6-dimethyldec-9-enoate (1408299-10-4) → (3S,6R,7S,12S)-12-(benzyloxymethyl)-6-(2-mehtoxyethoxy)-3,7-dimethyloxacyclododec-10-en-2-one (1408299-20-6) + (3S,6R,7S,12S)-12-(benzyloxymethyl)-6-(2-mehtoxyethoxy) (1408299-21-7)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In benzene; for 24h; Overall yield = 58 %; Overall yield = 0.092 g; Inert atmosphere; Reflux;

DOI:10.1016/j.tetasy.2012.07.006

Reference yield:

(S)-4-benzyl-3-((S)-2-methylpent-4-enoyl)oxazolidin-2-one (943856-58-4) → (3S,6R,7S,12S)-12-(benzyloxymethyl)-6-(2-mehtoxyethoxy)-3,7-dimethyloxacyclododec-10-en-2-one (1408299-20-6) + (3S,6R,7S,12S)-12-(benzyloxymethyl)-6-(2-mehtoxyethoxy) (1408299-21-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C

2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

2.2: 2 h / 0 - 20 °C

3.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / 0 °C

3.2: 16 h / 20 °C

4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

5.1: di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.17 h / 0 °C

5.2: 0.5 h / 0 °C

5.3: 1 h / 0 °C

6.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C

7.1: dmap; triethylamine / dichloromethane / 20 h / 0 - 20 °C

8.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

10.1: ammonia; lithium / tetrahydrofuran / 1 h / -78 °C

11.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C

12.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 °C

12.2: 6 h / 20 °C

13.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / benzene / 24 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; dimethylsulfide borane complex; di-n-butylboryl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; ammonia; lithium; sodium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene; 5.1: |Evans Aldol Reaction / 5.2: |Evans Aldol Reaction / 10.1: |Birch Reduction;

DOI:10.1016/j.tetasy.2012.07.006

Reference yield:

(2S,5R,6S)-1-(benzyloxy)-2,6-dimethyldec-9-en-5-ol (1408299-04-6) → (3S,6R,7S,12S)-12-(benzyloxymethyl)-6-(2-mehtoxyethoxy)-3,7-dimethyloxacyclododec-10-en-2-one (1408299-20-6) + (3S,6R,7S,12S)-12-(benzyloxymethyl)-6-(2-mehtoxyethoxy) (1408299-21-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

2.1: ammonia; lithium / tetrahydrofuran / 1 h / -78 °C

3.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C

4.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 °C

4.2: 6 h / 20 °C

5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / benzene / 24 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dipyridinium dichromate; 2,4,6-trichlorobenzoyl chloride; ammonia; lithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene; 2.1: |Birch Reduction;

DOI:10.1016/j.tetasy.2012.07.006

upstream raw materials:

(S)-4-benzyl-3-((S)-2-methylpent-4-enoyl)oxazolidin-2-one

(S)-5-(benzyloxy)-4-methylpentan-1-ol

(S)-(-)-2-methyl-4-penten-1-ol

(4S)-4-benzyl-3-(hex-5-enoyl)-1,3-oxazolidin-2-one