(Z)-5-[(1S,2R,3aS,7aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(dimethyl-phenyl-silanyl)-2-(tetrahydro-pyran-2-yloxy)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-pent-4-enoic acid methyl ester

Base Information

Chemical Name:(Z)-5-[(1S,2R,3aS,7aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(dimethyl-phenyl-silanyl)-2-(tetrahydro-pyran-2-yloxy)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-pent-4-enoic acid methyl ester
CAS No.:113208-28-9
Molecular Formula:C₃₅H₅₆O₅Si₂
Molecular Weight:612.998
Hs Code.:

(Z)-5-[(1S,2R,3aS,7aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(dimethyl-phenyl-silanyl)-2-(tetrahydro-pyran-2-yloxy)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-pent-4-enoic acid methyl ester

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Chemical Property of (Z)-5-[(1S,2R,3aS,7aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(dimethyl-phenyl-silanyl)-2-(tetrahydro-pyran-2-yloxy)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-pent-4-enoic acid methyl ester

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Technology Process of (Z)-5-[(1S,2R,3aS,7aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(dimethyl-phenyl-silanyl)-2-(tetrahydro-pyran-2-yloxy)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-pent-4-enoic acid methyl ester

There total 10 articles about (Z)-5-[(1S,2R,3aS,7aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(dimethyl-phenyl-silanyl)-2-(tetrahydro-pyran-2-yloxy)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-pent-4-enoic acid methyl ester 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:

: 65025-95-8
(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

: 113208-28-9,113331-57-0,113331-58-1,114290-01-6,114290-02-7
(Z)-5-[(1S,2R,3aS,7aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(dimethyl-phenyl-silanyl)-2-(tetrahydro-pyran-2-yloxy)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-pent-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: DIBAH / toluene / -78 °C

2: toluene / 60 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C

4: Zn, TiCl₄ / Ambient temperature

5: 1.)Siam₂BH, 2.) 30percent H₂O₂, 6N NaOH / 1.) THF, 0 deg C, 2.) THF, 0 deg C

6: 98 percent / LiAlH₄ / tetrahydrofuran / 0 °C

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C

8: dibenzylammonium trifluoroacetate / toluene / 110 °C

9: 1.) t-BuOK / THF, RT

10: diethyl ether / 0 °C

With sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; potassium tert-butylate; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; titanium tetrachloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; zinc; dibenzylammonium trifluoroacetate salt; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1016/S0040-4039(00)96003-9

Reference yield:

: 113428-17-4
(E)-4-[(1R,2S,3R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-but-2-enoic acid methyl ester

: 113208-28-9,113331-57-0,113331-58-1,114290-01-6,114290-02-7
(Z)-5-[(1S,2R,3aS,7aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(dimethyl-phenyl-silanyl)-2-(tetrahydro-pyran-2-yloxy)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-pent-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.)Siam₂BH, 2.) 30percent H₂O₂, 6N NaOH / 1.) THF, 0 deg C, 2.) THF, 0 deg C

2: 98 percent / LiAlH₄ / tetrahydrofuran / 0 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C

4: dibenzylammonium trifluoroacetate / toluene / 110 °C

5: 1.) t-BuOK / THF, RT

6: diethyl ether / 0 °C

With sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; potassium tert-butylate; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; dimethyl sulfoxide; triethylamine; dibenzylammonium trifluoroacetate salt; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1016/S0040-4039(00)96003-9

Reference yield:

: 123536-33-4
(E)-4-[(1R,2S,3R,5S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-but-2-enoic acid methyl ester

: 113208-28-9,113331-57-0,113331-58-1,114290-01-6,114290-02-7
(Z)-5-[(1S,2R,3aS,7aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(dimethyl-phenyl-silanyl)-2-(tetrahydro-pyran-2-yloxy)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-pent-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C

2: Zn, TiCl₄ / Ambient temperature

3: 1.)Siam₂BH, 2.) 30percent H₂O₂, 6N NaOH / 1.) THF, 0 deg C, 2.) THF, 0 deg C

4: 98 percent / LiAlH₄ / tetrahydrofuran / 0 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C

6: dibenzylammonium trifluoroacetate / toluene / 110 °C

7: 1.) t-BuOK / THF, RT

8: diethyl ether / 0 °C

With sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; potassium tert-butylate; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; titanium tetrachloride; dimethyl sulfoxide; triethylamine; zinc; dibenzylammonium trifluoroacetate salt; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1016/S0040-4039(00)96003-9