(3S,5R,7S)-7-benzyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-1,3,5,9-tetraol

Base Information

Chemical Name:(3S,5R,7S)-7-benzyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-1,3,5,9-tetraol
CAS No.:1352746-48-5
Molecular Formula:C₂₁H₃₄O₅
Molecular Weight:366.498
Hs Code.:

Synonyms:(3S,5R,7S)-7-benzyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-1,3,5,9-tetraol

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Chemical Property of (3S,5R,7S)-7-benzyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-1,3,5,9-tetraol

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Technology Process of (3S,5R,7S)-7-benzyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-1,3,5,9-tetraol

There total 7 articles about (3S,5R,7S)-7-benzyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-1,3,5,9-tetraol 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: 99.0%

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

: 1352746-48-5
(3S,5R,7S)-7-benzyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-1,3,5,9-tetraol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.064

Reference yield:

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

: 1352746-48-5
(3S,5R,7S)-7-benzyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-1,3,5,9-tetraol

Guidance literature:: Multi-step reaction with 2 steps

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

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; In tetrahydrofuran;
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

: 1352746-48-5
(3S,5R,7S)-7-benzyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-1,3,5,9-tetraol

Guidance literature:: Multi-step reaction with 3 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

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

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