(2S,3S,5R,7S,9S,11S,13R,15S)-3-(benzyloxy)-9-((tert-butyldiphenylsilyloxy)methyl)-2-(1'-(4-methoxybenzyloxy)ethan-2'-yl)-11-methoxy-13-methoxy-15-methyl-1,6,8-trioxadispiro[4.1.5.3]pentadecane

Base Information

Chemical Name:(2S,3S,5R,7S,9S,11S,13R,15S)-3-(benzyloxy)-9-((tert-butyldiphenylsilyloxy)methyl)-2-(1'-(4-methoxybenzyloxy)ethan-2'-yl)-11-methoxy-13-methoxy-15-methyl-1,6,8-trioxadispiro[4.1.5.3]pentadecane
CAS No.:1339911-25-9
Molecular Formula:C₄₉H₆₄O₉Si
Molecular Weight:825.127
Hs Code.:

(2S,3S,5R,7S,9S,11S,13R,15S)-3-(benzyloxy)-9-((tert-butyldiphenylsilyloxy)methyl)-2-(1'-(4-methoxybenzyloxy)ethan-2'-yl)-11-methoxy-13-methoxy-15-methyl-1,6,8-trioxadispiro[4.1.5.3]pentadecane

Synonyms:(2S,3S,5R,7S,9S,11S,13R,15S)-3-(benzyloxy)-9-((tert-butyldiphenylsilyloxy)methyl)-2-(1'-(4-methoxybenzyloxy)ethan-2'-yl)-11-methoxy-13-methoxy-15-methyl-1,6,8-trioxadispiro[4.1.5.3]pentadecane

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Chemical Property of (2S,3S,5R,7S,9S,11S,13R,15S)-3-(benzyloxy)-9-((tert-butyldiphenylsilyloxy)methyl)-2-(1'-(4-methoxybenzyloxy)ethan-2'-yl)-11-methoxy-13-methoxy-15-methyl-1,6,8-trioxadispiro[4.1.5.3]pentadecane

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Technology Process of (2S,3S,5R,7S,9S,11S,13R,15S)-3-(benzyloxy)-9-((tert-butyldiphenylsilyloxy)methyl)-2-(1'-(4-methoxybenzyloxy)ethan-2'-yl)-11-methoxy-13-methoxy-15-methyl-1,6,8-trioxadispiro[4.1.5.3]pentadecane

There total 22 articles about (2S,3S,5R,7S,9S,11S,13R,15S)-3-(benzyloxy)-9-((tert-butyldiphenylsilyloxy)methyl)-2-(1'-(4-methoxybenzyloxy)ethan-2'-yl)-11-methoxy-13-methoxy-15-methyl-1,6,8-trioxadispiro[4.1.5.3]pentadecane 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: 62.0%

: 1339911-31-7
(1R,3S)-3-(2-((2'S,3'S)-2'-(benzyloxy)-3'-hydroxy-5'-(4-methoxybenzyloxy)-pentan-1'-yl)-1,3-dithian-2-yl)-1-(2-((2''S,4''S)-5''-(tert-butyldiphenylsilyloxy)-4''-hydroxy-2''-methoxypentan-1''-yl)-1,3-dithian-2-yl)-1-methoxybutane

: 1339911-25-9
(2S,3S,5R,7S,9S,11S,13R,15S)-3-(benzyloxy)-9-((tert-butyldiphenylsilyloxy)methyl)-2-(1'-(4-methoxybenzyloxy)ethan-2'-yl)-11-methoxy-13-methoxy-15-methyl-1,6,8-trioxadispiro[4.1.5.3]pentadecane

Guidance literature:: With mercury dichloride; In water; acetonitrile; at 0 ℃; for 5h;
DOI:10.1021/jo201729t

Reference yield:

: 1029083-72-4
(2S,3S)-5-(4-methoxybenzyloxy)-3-methylpentane-1,2-diol

: 1339911-25-9
(2S,3S,5R,7S,9S,11S,13R,15S)-3-(benzyloxy)-9-((tert-butyldiphenylsilyloxy)methyl)-2-(1'-(4-methoxybenzyloxy)ethan-2'-yl)-11-methoxy-13-methoxy-15-methyl-1,6,8-trioxadispiro[4.1.5.3]pentadecane

Guidance literature:: Multi-step reaction with 12 steps

1.1: sodium periodate / tetrahydrofuran; water / 20 °C

2.1: cobalt(II) chloride hexahydrate / acetonitrile / 2 h / 20 °C

3.1: dimethylsulfide; boron trifluoride diethyl etherate / dichloromethane / 0.33 h / 20 °C

4.1: dmap; triethylamine / dichloromethane / 2.5 h / 20 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / 20 °C / Inert atmosphere

5.2: 0.17 h / 20 °C / Inert atmosphere

6.1: potassium hydride / tetrahydrofuran; mineral oil / 5 h / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

8.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.33 h / 20 °C / Molecular sieve

9.1: n-butyllithium; dibutylmagnesium / tetrahydrofuran; hexane; n-heptane / 0.33 h / 20 °C

9.2: 0.17 h / 20 °C

10.1: potassium hydride / tetrahydrofuran; mineral oil / 20 °C / Inert atmosphere

11.1: pyridinium p-toluenesulfonate / tert-butyl alcohol / 5.5 h / Reflux

12.1: mercury dichloride / water; acetonitrile / 5 h / 0 °C

With dmap; sodium periodate; n-butyllithium; tetrapropylammonium perruthennate; cobalt(II) chloride hexahydrate; dimethylsulfide; boron trifluoride diethyl etherate; dibutylmagnesium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hydride; 4-methylmorpholine N-oxide; triethylamine; mercury dichloride; In tetrahydrofuran; hexane; n-heptane; dichloromethane; water; acetonitrile; mineral oil; tert-butyl alcohol;
DOI:10.1021/jo201729t

Reference yield:

: 1235570-41-8
(S)-3-(2-((2'S,3'S)-2'-(benzyloxy)-3'-(ethoxymethoxy)-5'-(4-methoxybenzyloxy)pentane-1'-yl)-1,3-dithian-2-yl)butanal

: 1339911-25-9
(2S,3S,5R,7S,9S,11S,13R,15S)-3-(benzyloxy)-9-((tert-butyldiphenylsilyloxy)methyl)-2-(1'-(4-methoxybenzyloxy)ethan-2'-yl)-11-methoxy-13-methoxy-15-methyl-1,6,8-trioxadispiro[4.1.5.3]pentadecane

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium; dibutylmagnesium / tetrahydrofuran; hexane; n-heptane / 0.33 h / 20 °C

1.2: 0.17 h / 20 °C

2.1: potassium hydride / tetrahydrofuran; mineral oil / 20 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / tert-butyl alcohol / 5.5 h / Reflux

4.1: mercury dichloride / water; acetonitrile / 5 h / 0 °C

With n-butyllithium; dibutylmagnesium; pyridinium p-toluenesulfonate; potassium hydride; mercury dichloride; In tetrahydrofuran; hexane; n-heptane; water; acetonitrile; mineral oil; tert-butyl alcohol;
DOI:10.1021/jo201729t