(3S,5R,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-3,5-diol

Base Information

Chemical Name:(3S,5R,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-3,5-diol
CAS No.:1352746-47-4
Molecular Formula:C₄₃H₆₆O₅Si₂
Molecular Weight:719.165
Hs Code.:

Synonyms:(3S,5R,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-3,5-diol

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Chemical Property of (3S,5R,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-3,5-diol

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Technology Process of (3S,5R,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-3,5-diol

There total 7 articles about (3S,5R,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-3,5-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: 93.0%

: 1352746-46-3
(3S,5R,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-8,8-dimethylnonane-3,5-diol

: 77-76-9
2,2-dimethoxy-propane

: 1352746-47-4
(3S,5R,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-3,5-diol

Guidance literature:: With pyridinium p-toluenesulfonate; at 20 ℃; for 18h; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.064

Reference yield:

: 470470-80-5
(5S,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one

: 1352746-47-4
(3S,5R,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-3,5-diol

Guidance literature:: Multi-step reaction with 2 steps

1: lithium tri-t-butoxyaluminum hydride; lithium iodide / tetrahydrofuran; diethyl ether / 18 h / -78 °C / Inert atmosphere

2: pyridinium p-toluenesulfonate / 18 h / 20 °C / Inert atmosphere

With pyridinium p-toluenesulfonate; lithium tri-t-butoxyaluminum hydride; lithium iodide; In tetrahydrofuran; diethyl ether;
DOI:10.1016/j.tet.2011.09.064

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1352746-47-4
(3S,5R,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-3,5-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1H-imidazole; dmap; tetra-(n-butyl)ammonium iodide / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.1: borane / tetrahydrofuran / -18 - 20 °C / Inert atmosphere

2.2: 3 h / 50 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

4.2: 0.03 h / -78 °C / Inert atmosphere

5.1: lithium tri-t-butoxyaluminum hydride; lithium iodide / tetrahydrofuran; diethyl ether / 18 h / -78 °C / Inert atmosphere

6.1: pyridinium p-toluenesulfonate / 18 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; oxalyl dichloride; borane; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; lithium tri-t-butoxyaluminum hydride; diisopropylamine; lithium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 4.2: Aldol condensation;
DOI:10.1016/j.tet.2011.09.064