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

Base Information

• Chemical Name: (3R,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one
• CAS No.: 1123785-59-0
• Molecular Formula: C₂₇H₄₄O₄Si
• Molecular Weight: 460.729

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

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

Chemical Property:

Purity/Quality:

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MSDS Files:

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

There total 21 articles about (3R,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-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,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-11-hydroxy-2,6-dimethyldodec-9-enoic acid (1123785-57-8) → (3S,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one (1123785-03-4) + (3R,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one (1123785-59-0)

Guidance literature:

(2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-11-hydroxy-2,6-dimethyldodec-9-enoic acid; With 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃;

With dmap; In benzene; at 80 ℃;

DOI:10.1016/j.tetlet.2008.11.088

Reference yield:

(S)-4-benzyl-3-((S)-2-methylpent-4-enoyl)oxazolidin-2-one (943856-58-4) → (3S,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one (1123785-03-4) + (3R,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one (1123785-59-0)

Guidance literature:

Multi-step reaction with 20 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: 2,6-dimethylpyridine / 0.5 h / 0 °C

7.1: sodium tetrahydroborate; lithium chloride / tetrahydrofuran; ethanol / 6 h / 20 °C

8.1: dipyridinium dichromate / dichloromethane / 20 °C

9.1: ethyl (triphenylphosphoranylidene)acetate / benzene / 24 h / 20 °C

10.1: nickel(II) chloride hexahydrate; sodium hydride / methanol / 0.5 h / 0 °C

11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C

12.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h / 0 °C

13.1: hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / ethanol / 0 °C

14.1: potassium hexamethylsilazane / 1,2-dimethoxyethane; toluene / 0.5 h / -60 °C

14.2: 2 h / -60 °C

15.1: zinc(II) nitrate hexahydrate / acetonitrile / 6 h / 50 °C

16.1: ammonia; lithium / tetrahydrofuran-d8 / 1 h / -78 °C

17.1: di(n-butyl)tin oxide / toluene / 4 h / Reflux

17.2: 2 h / Reflux

18.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 3 h / 20 °C

19.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 3 h / 0 °C

20.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C

20.2: 11 h / 80 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; lithium aluminium tetrahydride; dipyridinium dichromate; 2-methyl-but-2-ene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; zinc(II) nitrate hexahydrate; nickel(II) chloride hexahydrate; hexaammonium heptamolybdate tetrahydrate; [bis(acetoxy)iodo]benzene; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; di-n-butylboryl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; ammonia; dihydrogen peroxide; lithium; potassium hexamethylsilazane; sodium hydride; di(n-butyl)tin oxide; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; ethyl (triphenylphosphoranylidene)acetate; lithium chloride; In tetrahydrofuran; methanol; tetrahydrofuran-d8; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; benzene; 5.1: |Evans Aldol Reaction / 5.2: |Evans Aldol Reaction / 14.1: |Julia-Kocienski Olefination / 14.2: |Julia-Kocienski Olefination / 16.1: |Birch Reduction;

DOI:10.1016/j.tetasy.2012.07.006

Reference yield:

(2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethyldodec-9-en-1,11-diol (1123785-54-5) → (3S,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one (1123785-03-4) + (3R,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one (1123785-59-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 3 h / 20 °C

2.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 3 h / 0 °C

3.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C

3.2: 11 h / 80 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/j.tetasy.2012.07.006

upstream raw materials:

(2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-11-hydroxy-2,6-dimethyldodec-9-enoic acid

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

(4R,5R,8S,)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnonan-1-ol

5-((4R,5R,8S,)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnonylsulfonyl)-1-phenyl-1H-tetrazole

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