(1R,3aR,4R,5S,7aR)-4-{(S)-[4-(benzyldimethylsilyl)phenyl](hydroxy)methyl}-5-ethynyl-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-1-ol

Base Information

Chemical Name:(1R,3aR,4R,5S,7aR)-4-{(S)-[4-(benzyldimethylsilyl)phenyl](hydroxy)methyl}-5-ethynyl-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-1-ol
CAS No.:1531626-61-5
Molecular Formula:C₃₁H₄₀O₂Si
Molecular Weight:472.743
Hs Code.:

Synonyms:(1R,3aR,4R,5S,7aR)-4-{(S)-[4-(benzyldimethylsilyl)phenyl](hydroxy)methyl}-5-ethynyl-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-1-ol

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Chemical Property of (1R,3aR,4R,5S,7aR)-4-{(S)-[4-(benzyldimethylsilyl)phenyl](hydroxy)methyl}-5-ethynyl-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-1-ol

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Technology Process of (1R,3aR,4R,5S,7aR)-4-{(S)-[4-(benzyldimethylsilyl)phenyl](hydroxy)methyl}-5-ethynyl-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-1-ol

There total 16 articles about (1R,3aR,4R,5S,7aR)-4-{(S)-[4-(benzyldimethylsilyl)phenyl](hydroxy)methyl}-5-ethynyl-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-1-ol 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: 78.0%

: 1531626-58-0
[4-(benzyldimethylsilyl)phenyl][(1R,3aS,4R,5S,7aR)-5-ethynyl-1-hydroxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl]methanone

: 1531626-61-5
(1R,3aR,4R,5S,7aR)-4-{(S)-[4-(benzyldimethylsilyl)phenyl](hydroxy)methyl}-5-ethynyl-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-1-ol

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; methanol;
DOI:10.1021/ol403441c

Reference yield:

: 1309113-14-1
(E)-tert-butyl[(6-{[(4-methoxybenzyl)oxy]methyl}-4,4-dimethylhepta-2,6-dien-1-yl)oxy]dimethylsilane

: 1531626-61-5
(1R,3aR,4R,5S,7aR)-4-{(S)-[4-(benzyldimethylsilyl)phenyl](hydroxy)methyl}-5-ethynyl-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-1-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C

2.1: titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane / 20 h / -25 °C

2.2: Molecular sieve

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h

4.1: PPTA / dichloromethane / 2 h / 20 °C

4.2: -78 - 20 °C

5.1: dmap; sodium hydrogencarbonate / dichloromethane / 3 h / 0 °C

6.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C

6.2: -78 - 20 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

8.1: NMO; tetrapropylammonium perruthennate / dichloromethane / 3 h / -30 °C / Molecular sieve

8.2: 0.42 h / -90 - -70 °C

9.1: tetrapropylammonium perruthennate; magnesium bromide ethyl etherate / dichloromethane / 3 h / 0 °C

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.83 h / 0 °C / pH 7

11.1: sodium tetrahydroborate / methanol; tetrahydrofuran

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; NMO; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydrogencarbonate; magnesium bromide ethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol403441c

Reference yield:

: 1309113-16-3
(E)-7-[(tert-butyldimethylsilyl)oxy]-4,4-dimethyl-2-methylenehept-5-en-1-ol

: 1531626-61-5
(1R,3aR,4R,5S,7aR)-4-{(S)-[4-(benzyldimethylsilyl)phenyl](hydroxy)methyl}-5-ethynyl-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-1-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane / 20 h / -25 °C

1.2: Molecular sieve

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h

3.1: PPTA / dichloromethane / 2 h / 20 °C

3.2: -78 - 20 °C

4.1: dmap; sodium hydrogencarbonate / dichloromethane / 3 h / 0 °C

5.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C

5.2: -78 - 20 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

7.1: NMO; tetrapropylammonium perruthennate / dichloromethane / 3 h / -30 °C / Molecular sieve

7.2: 0.42 h / -90 - -70 °C

8.1: tetrapropylammonium perruthennate; magnesium bromide ethyl etherate / dichloromethane / 3 h / 0 °C

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.83 h / 0 °C / pH 7

10.1: sodium tetrahydroborate / methanol; tetrahydrofuran

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; NMO; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydrogencarbonate; magnesium bromide ethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol403441c