(1S,3R,5R,7R,9S,13S,14S,15S)-9-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methoxy-5,8,8,14-tetramethyl-15-((triisopropylsilyl)oxy)-10,17,18-trioxatricyclo[11.3.1.13,7]octadecane-4,11-dione

Base Information

Chemical Name:(1S,3R,5R,7R,9S,13S,14S,15S)-9-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methoxy-5,8,8,14-tetramethyl-15-((triisopropylsilyl)oxy)-10,17,18-trioxatricyclo[11.3.1.13,7]octadecane-4,11-dione
CAS No.:1381848-86-7
Molecular Formula:C₄₆H₇₂O₈Si₂
Molecular Weight:809.244
Hs Code.:

(1S,3R,5R,7R,9S,13S,14S,15S)-9-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methoxy-5,8,8,14-tetramethyl-15-((triisopropylsilyl)oxy)-10,17,18-trioxatricyclo[11.3.1.13,7]octadecane-4,11-dione

Synonyms:(1S,3R,5R,7R,9S,13S,14S,15S)-9-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methoxy-5,8,8,14-tetramethyl-15-((triisopropylsilyl)oxy)-10,17,18-trioxatricyclo[11.3.1.13,7]octadecane-4,11-dione

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Chemical Property of (1S,3R,5R,7R,9S,13S,14S,15S)-9-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methoxy-5,8,8,14-tetramethyl-15-((triisopropylsilyl)oxy)-10,17,18-trioxatricyclo[11.3.1.13,7]octadecane-4,11-dione

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Technology Process of (1S,3R,5R,7R,9S,13S,14S,15S)-9-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methoxy-5,8,8,14-tetramethyl-15-((triisopropylsilyl)oxy)-10,17,18-trioxatricyclo[11.3.1.13,7]octadecane-4,11-dione

There total 37 articles about (1S,3R,5R,7R,9S,13S,14S,15S)-9-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methoxy-5,8,8,14-tetramethyl-15-((triisopropylsilyl)oxy)-10,17,18-trioxatricyclo[11.3.1.13,7]octadecane-4,11-dione 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%

: 1381848-85-6
2-((2S,3S,4S,6S)-6-(((2R,4R,6R)-6-((S)-4-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-2-methylbutan-2-yl)-2-methoxy-4-methyl-3-oxotetrahydro-2H-pyran-2-yl)methyl)-3-methyl-4-((triisopropylsilyl)oxy)tetrahydro-2H-pyran-2-yl)acetic acid

: 1381848-86-7
(1S,3R,5R,7R,9S,13S,14S,15S)-9-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methoxy-5,8,8,14-tetramethyl-15-((triisopropylsilyl)oxy)-10,17,18-trioxatricyclo[11.3.1.13,7]octadecane-4,11-dione

Guidance literature:: With pyridine; pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide; In 1,2-dichloro-ethane; for 2h; Reflux;
DOI:10.1021/ol301278e

Reference yield:

: 1381848-71-0
(4R,6R)-6-((S)-4-((tert-butyldiphenylsilyl)oxy)-2-methyl-3-((triethylsilyl)oxy)butan-2-yl)-4-methyltetrahydro-2H-pyran-2-one

: 1381848-86-7
(1S,3R,5R,7R,9S,13S,14S,15S)-9-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methoxy-5,8,8,14-tetramethyl-15-((triisopropylsilyl)oxy)-10,17,18-trioxatricyclo[11.3.1.13,7]octadecane-4,11-dione

Guidance literature:: Multi-step reaction with 8 steps

1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.42 h / -78 °C

1.2: 0.5 h / -78 °C

2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 0 - 20 °C

2.2: 0.67 h

2.3: 14 h / 20 °C

3.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / methanol; dichloromethane / 1.5 h / 0 °C

4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 27 h / 0 - 20 °C / Molecular sieve

5.1: camphor-10-sulfonic acid / methanol; dichloromethane / 2.5 h / 0 °C

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1.5 h / 20 °C

7.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 6.5 h / 20 °C

8.1: pyridine; pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide / 1,2-dichloro-ethane / 2 h / Reflux

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrapropylammonium perruthennate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 9-bora-bicyclo[3.3.1]nonane; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; toluene;
DOI:10.1021/ol301278e

Reference yield:

: 1381848-73-2
(2R,4R)-2-((S)-4-((tert-butyldiphenylsilyl)oxy)-2-methyl-3-((triethylsilyl)oxy)butan-2-yl)-4-methyl-3,4-dihydro-2H-pyran-6-yl trifluoromethanesulfonate

: 1381848-86-7
(1S,3R,5R,7R,9S,13S,14S,15S)-9-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methoxy-5,8,8,14-tetramethyl-15-((triisopropylsilyl)oxy)-10,17,18-trioxatricyclo[11.3.1.13,7]octadecane-4,11-dione

Guidance literature:: Multi-step reaction with 7 steps

1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 0 - 20 °C

1.2: 0.67 h

1.3: 14 h / 20 °C

2.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / methanol; dichloromethane / 1.5 h / 0 °C

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 27 h / 0 - 20 °C / Molecular sieve

4.1: camphor-10-sulfonic acid / methanol; dichloromethane / 2.5 h / 0 °C

5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1.5 h / 20 °C

6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 6.5 h / 20 °C

7.1: pyridine; pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide / 1,2-dichloro-ethane / 2 h / Reflux

With pyridine; tetrapropylammonium perruthennate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 9-bora-bicyclo[3.3.1]nonane; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane;
DOI:10.1021/ol301278e