(5S,7S)-7-benzyloxy-10-{(7R,9R)-9-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-(tert-butyldiphenylsilyloxy)-5-hydroxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecan-3-one

Base Information

Chemical Name:(5S,7S)-7-benzyloxy-10-{(7R,9R)-9-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-(tert-butyldiphenylsilyloxy)-5-hydroxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecan-3-one
CAS No.:1352746-41-8
Molecular Formula:C₅₅H₈₈O₁₀Si₃
Molecular Weight:993.554
Hs Code.:

(5S,7S)-7-benzyloxy-10-{(7R,9R)-9-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-(tert-butyldiphenylsilyloxy)-5-hydroxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecan-3-one

Synonyms:(5S,7S)-7-benzyloxy-10-{(7R,9R)-9-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-(tert-butyldiphenylsilyloxy)-5-hydroxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecan-3-one

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Chemical Property of (5S,7S)-7-benzyloxy-10-{(7R,9R)-9-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-(tert-butyldiphenylsilyloxy)-5-hydroxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecan-3-one

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Technology Process of (5S,7S)-7-benzyloxy-10-{(7R,9R)-9-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-(tert-butyldiphenylsilyloxy)-5-hydroxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecan-3-one

There total 7 articles about (5S,7S)-7-benzyloxy-10-{(7R,9R)-9-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-(tert-butyldiphenylsilyloxy)-5-hydroxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecan-3-one 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: 60.0%

: 1352746-40-7
(7R,9R)-9-[(4S)-4-benzyloxy-3,3-dimethyl-5-formyl-2-(trimethylsilylethoxy)methoxypentyl]-7-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]decane

: 97250-25-4
tert-Butyldiphenylsilyl β-hydroxybutanone

: 1352746-41-8
(5S,7S)-7-benzyloxy-10-{(7R,9R)-9-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-(tert-butyldiphenylsilyloxy)-5-hydroxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecan-3-one

Guidance literature:: tert-Butyldiphenylsilyl β-hydroxybutanone; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

(7R,9R)-9-[(4S)-4-benzyloxy-3,3-dimethyl-5-formyl-2-(trimethylsilylethoxy)methoxypentyl]-7-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]decane; In tetrahydrofuran; hexane; at -78 ℃; for 0.0333333h; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.064

Reference yield:

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

: 1352746-41-8
(5S,7S)-7-benzyloxy-10-{(7R,9R)-9-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-(tert-butyldiphenylsilyloxy)-5-hydroxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecan-3-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

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

2.2: 3 h / 20 °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

With n-butyllithium; oxalyl dichloride; borane; dimethyl sulfoxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 4.2: Aldol condensation;
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

: 1352746-41-8
(5S,7S)-7-benzyloxy-10-{(7R,9R)-9-tert-butyldimethylsilyloxymethyl-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-(tert-butyldiphenylsilyloxy)-5-hydroxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecan-3-one

Guidance literature:: Multi-step reaction with 5 steps

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

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

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

3.2: 3 h / 20 °C

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

4.2: -78 - 20 °C / Inert atmosphere

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

5.2: 0.03 h / -78 °C / Inert atmosphere

With n-butyllithium; oxalyl dichloride; borane; lithium triethylborohydride; dimethyl sulfoxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 5.2: Aldol condensation;
DOI:10.1016/j.tet.2011.09.064