(7R,9R)-9-[(4S)-4-benzyloxy-3,3-dimethyl-2,6-dihydroxyhexyl]-7-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]decane

Base Information

Chemical Name:(7R,9R)-9-[(4S)-4-benzyloxy-3,3-dimethyl-2,6-dihydroxyhexyl]-7-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]decane
CAS No.:1352746-35-0
Molecular Formula:C₂₉H₅₀O₇Si
Molecular Weight:538.797
Hs Code.:

Synonyms:(7R,9R)-9-[(4S)-4-benzyloxy-3,3-dimethyl-2,6-dihydroxyhexyl]-7-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]decane

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Chemical Property of (7R,9R)-9-[(4S)-4-benzyloxy-3,3-dimethyl-2,6-dihydroxyhexyl]-7-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]decane

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Technology Process of (7R,9R)-9-[(4S)-4-benzyloxy-3,3-dimethyl-2,6-dihydroxyhexyl]-7-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]decane

There total 4 articles about (7R,9R)-9-[(4S)-4-benzyloxy-3,3-dimethyl-2,6-dihydroxyhexyl]-7-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]decane 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: 58.0%

: (7R,9R)-9-[(4S)-4-benzyloxy-3,3-dimethyl-2-hydroxyhex-5-enyl]-7-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]decane

: 1352746-35-0
(7R,9R)-9-[(4S)-4-benzyloxy-3,3-dimethyl-2,6-dihydroxyhexyl]-7-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]decane

Guidance literature:: (7R,9R)-9-[(4S)-4-benzyloxy-3,3-dimethyl-2-hydroxyhex-5-enyl]-7-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]decane; With borane; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 1h;
DOI:10.1016/j.tet.2011.09.064

Reference yield:

: 1352746-32-7
(7R,9R)-9-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-7-tert-butyldimethysilyloxymethyl-1,4,8-trioxaspiro[4.5]-decane

: 1352746-35-0
(7R,9R)-9-[(4S)-4-benzyloxy-3,3-dimethyl-2,6-dihydroxyhexyl]-7-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]decane

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium triethylborohydride / tetrahydrofuran / -78 - 20 °C

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

2.2: 1 h / 20 °C

With borane; lithium triethylborohydride; In tetrahydrofuran;
DOI:10.1016/j.tet.2011.09.064

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1352746-35-0
(7R,9R)-9-[(4S)-4-benzyloxy-3,3-dimethyl-2,6-dihydroxyhexyl]-7-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]decane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1H-imidazole / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.1: lithium triethylborohydride / tetrahydrofuran / -78 - 20 °C

3.1: borane / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

3.2: 1 h / 20 °C

With 1H-imidazole; borane; lithium triethylborohydride; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2011.09.064