(2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethyldodec-9-en-1,11-diol

Base Information

Chemical Name:(2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethyldodec-9-en-1,11-diol
CAS No.:1123785-54-5
Molecular Formula:C₂₇H₄₈O₄Si
Molecular Weight:464.761
Hs Code.:

Synonyms:(2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethyldodec-9-en-1,11-diol

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Chemical Property of (2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethyldodec-9-en-1,11-diol

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Technology Process of (2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethyldodec-9-en-1,11-diol

There total 13 articles about (2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethyldodec-9-en-1,11-diol 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: 84.0%

: 1123785-51-2
(2S,7R,8R,11S,3E)-8-(tert-butyldimethylsilyloxy)-7,11-dimethyldodec-3-en-1,2,12-triol

: 100-39-0
benzyl bromide

: 1123785-54-5
(2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethyldodec-9-en-1,11-diol

Guidance literature:: With tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; In toluene; regioselective reaction; Reflux;
DOI:10.1016/j.tetlet.2008.11.088

Reference yield:

: 887706-39-0
(S)-5-(benzyloxy)-4-methylpentan-1-ol

: 1123785-54-5
(2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethyldodec-9-en-1,11-diol

Guidance literature:: Multi-step reaction with 14 steps

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

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

2.2: 0.5 h / 0 °C

2.3: 1 h / 0 °C

3.1: 2,6-dimethylpyridine / 0.5 h / 0 °C

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

5.1: dipyridinium dichromate / dichloromethane / 20 °C

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

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

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

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

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

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

11.2: 2 h / -60 °C

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

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

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

14.2: 2 h / Reflux

With 2,6-dimethylpyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; zinc(II) nitrate hexahydrate; nickel(II) chloride hexahydrate; hexaammonium heptamolybdate tetrahydrate; di-isopropyl azodicarboxylate; di-n-butylboryl trifluoromethanesulfonate; ammonia; dihydrogen peroxide; lithium; potassium hexamethylsilazane; sodium hydride; di(n-butyl)tin oxide; Dess-Martin periodane; triphenylphosphine; ethyl (triphenylphosphoranylidene)acetate; lithium chloride; In tetrahydrofuran; methanol; tetrahydrofuran-d8; 1,2-dimethoxyethane; ethanol; dichloromethane; toluene; acetonitrile; benzene; 2.1: |Evans Aldol Reaction / 2.2: |Evans Aldol Reaction / 11.1: |Julia-Kocienski Olefination / 11.2: |Julia-Kocienski Olefination / 13.1: |Birch Reduction;
DOI:10.1016/j.tetasy.2012.07.006

Reference yield:

: 1123785-76-1
C₃₁H₄₈N₄O₂SSi

: 1123785-54-5
(2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethyldodec-9-en-1,11-diol

Guidance literature:: Multi-step reaction with 5 steps

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

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

2.2: 2 h / -60 °C

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

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

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

5.2: 2 h / Reflux

With zinc(II) nitrate hexahydrate; hexaammonium heptamolybdate tetrahydrate; ammonia; dihydrogen peroxide; lithium; potassium hexamethylsilazane; di(n-butyl)tin oxide; In tetrahydrofuran-d8; 1,2-dimethoxyethane; ethanol; toluene; acetonitrile; 2.1: |Julia-Kocienski Olefination / 2.2: |Julia-Kocienski Olefination / 4.1: |Birch Reduction;
DOI:10.1016/j.tetasy.2012.07.006