(2S,3S,4S,5R,8S,6E)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-2,4,8-trimethyl-6-en-1-ol

Base Information

Chemical Name:(2S,3S,4S,5R,8S,6E)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-2,4,8-trimethyl-6-en-1-ol
CAS No.:1269830-06-9
Molecular Formula:C₄₂H₆₄O₅Si₂
Molecular Weight:705.138
Hs Code.:

Synonyms:(2S,3S,4S,5R,8S,6E)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-2,4,8-trimethyl-6-en-1-ol

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Chemical Property of (2S,3S,4S,5R,8S,6E)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-2,4,8-trimethyl-6-en-1-ol

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Technology Process of (2S,3S,4S,5R,8S,6E)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-2,4,8-trimethyl-6-en-1-ol

There total 7 articles about (2S,3S,4S,5R,8S,6E)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-2,4,8-trimethyl-6-en-1-ol 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: 52.0%

: 1269830-03-6
(6S,9R,10S,11S,7E)-11-[(S)-1-(benzyloxy)propan-2-yl]-9-(4-methoxybenzyloxy)-2,2,6,10,13,13,14,14-octamethyl-3,3-diphenyl-4,12-dioxa-3,13-disilapentadec-7-ene

: 1269830-06-9
(2S,3S,4S,5R,8S,6E)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-2,4,8-trimethyl-6-en-1-ol

Guidance literature:: With RANEY Ni; In ethanol; at 20 ℃;
DOI:10.1039/c0ob00491j

Reference yield:

: (3R,4S,5S)-6-(benzyloxy)-1-[(R)-tert-butylsulfinyl]-4-hydroxy-3,5-dimethylhexan-2-one

: 1269830-06-9
(2S,3S,4S,5R,8S,6E)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-2,4,8-trimethyl-6-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 3 h / -78 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C

2.2: 4 h / 0 °C

3.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C

4.1: 2,4,6-trimethyl-pyridine; trifluoroacetic anhydride / acetonitrile / 0.25 h / 0 °C

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 23 h / -78 - 20 °C

6.1: RANEY .(R). Ni / ethanol / 20 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; sodium hydride; diisobutylaluminium hydride; trifluoroacetic anhydride; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 4.1: Pummerer reaction;
DOI:10.1039/c0ob00491j

Reference yield:

: (2S,3R,4S,5S)-6-(benzyloxy)-1-[(R)-tert-butylsulfinyl]-3,5-dimethylhexane-2,4-diol

: 1269830-06-9
(2S,3S,4S,5R,8S,6E)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-2,4,8-trimethyl-6-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C

1.2: 4 h / 0 °C

2.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C

3.1: 2,4,6-trimethyl-pyridine; trifluoroacetic anhydride / acetonitrile / 0.25 h / 0 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 23 h / -78 - 20 °C

5.1: RANEY .(R). Ni / ethanol / 20 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; sodium hydride; trifluoroacetic anhydride; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3.1: Pummerer reaction;
DOI:10.1039/c0ob00491j