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

Base Information

Chemical Name:(3S,5R,7S)-7-benzyloxy-10-{(7R,9R)-9-(tert-butyldimethylsilyloxymethyl)-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecane-3,5-diol
CAS No.:1352746-43-0
Molecular Formula:C₅₅H₉₀O₁₀Si₃
Molecular Weight:995.57
Hs Code.:

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

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

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

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

There total 8 articles about (3S,5R,7S)-7-benzyloxy-10-{(7R,9R)-9-(tert-butyldimethylsilyloxymethyl)-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecane-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: 94.0%

: 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

: 1352746-43-0
(3S,5R,7S)-7-benzyloxy-10-{(7R,9R)-9-(tert-butyldimethylsilyloxymethyl)-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecane-3,5-diol

Guidance literature:: With acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at -40 - -20 ℃; 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

: 1352746-43-0
(3S,5R,7S)-7-benzyloxy-10-{(7R,9R)-9-(tert-butyldimethylsilyloxymethyl)-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecane-3,5-diol

Guidance literature:: Multi-step reaction with 5 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

5.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / -40 - -20 °C / Inert atmosphere

With n-butyllithium; oxalyl dichloride; borane; acetic acid; dimethyl sulfoxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 4.2: Aldol condensation;
DOI:10.1016/j.tet.2011.09.064

Reference yield:

: 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

: 1352746-43-0
(3S,5R,7S)-7-benzyloxy-10-{(7R,9R)-9-(tert-butyldimethylsilyloxymethyl)-1,4,8-trioxaspiro[4.5]dec-7-yl}-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-9-(2-trimethylsilylethoxy)methoxydecane-3,5-diol

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 0.03 h / -78 °C / Inert atmosphere

2.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / -40 - -20 °C / Inert atmosphere

With n-butyllithium; acetic acid; diisopropylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; hexane; acetonitrile; 1.2: Aldol condensation;
DOI:10.1016/j.tet.2011.09.064