[(1R,2R,3aS,9aR)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-5-yloxy]-acetic acid methyl ester

Base Information

Chemical Name:[(1R,2R,3aS,9aR)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-5-yloxy]-acetic acid methyl ester
CAS No.:120888-28-0
Molecular Formula:C₃₈H₄₈O₇Si
Molecular Weight:644.88
Hs Code.:

[(1R,2R,3aS,9aR)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-5-yloxy]-acetic acid methyl ester

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Chemical Property of [(1R,2R,3aS,9aR)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-5-yloxy]-acetic acid methyl ester

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Technology Process of [(1R,2R,3aS,9aR)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-5-yloxy]-acetic acid methyl ester

There total 22 articles about [(1R,2R,3aS,9aR)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-5-yloxy]-acetic 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: 48.0%

: 693-25-4
n-pentylmagnesium bromide

: 120888-27-9
[(1R,2R,3aS,9aR)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-3-oxo-propenyl)-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-5-yloxy]-acetic acid methyl ester

: 120888-28-0,120962-27-8
[(1R,2R,3aS,9aR)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-(R)-3-hydroxy-oct-1-enyl)-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-5-yloxy]-acetic acid methyl ester

: 120888-28-0,120962-27-8
[(1R,2R,3aS,9aR)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-5-yloxy]-acetic acid methyl ester

Guidance literature:: In tetrahydrofuran; at -78 ℃;
DOI:10.3987/COM-90-5370

Reference yield: 48.0%

: 693-25-4
n-pentylmagnesium bromide

: 120888-27-9
[(1R,2R,3aS,9aR)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-3-oxo-propenyl)-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-5-yloxy]-acetic acid methyl ester

: 120888-28-0,120962-27-8
[(1R,2R,3aS,9aR)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-(R)-3-hydroxy-oct-1-enyl)-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-5-yloxy]-acetic acid methyl ester

: 120888-28-0,120962-27-8
[(1R,2R,3aS,9aR)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-5-yloxy]-acetic acid methyl ester

Guidance literature:: In tetrahydrofuran; at -78 ℃;
DOI:10.3987/COM-90-5370

Reference yield:

: 120888-17-7
(1S,2R,3aS,9aR)-5-Methoxy-2-methoxymethoxy-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-1-ol

: 120888-28-0,120962-27-8
[(1R,2R,3aS,9aR)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((E)-(R)-3-hydroxy-oct-1-enyl)-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-5-yloxy]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) from -78 deg C to 0 deg C

2: 75 percent / benzene / 10 h / Irradiation

3: 99 percent / n-BuSLi / hexamethylphosphoric acid triamide / 0.5 h / 100 °C

4: 90 percent / NaH / 1,2-dimethoxy-ethane

5: 94 percent / BF₃*OEt₂, Me₂S / CH₂Cl₂ / 2 h / 0 °C

6: 97 percent / dimethylformamide; various solvent(s)

7: 1.) PhSeCl, 2.) pyridine, 30percent H₂O₂ / 1.) CCl₄, 0 deg C, 2.) RT, 1.5 h

8: 80 percent / 18-Crown-6 / toluene / 24 h / Heating

9: 1.) MeOH, K₂CO₃, 2.) CH₂N₂ / 1.) CH₂Cl₂, RT, 2 h, 2.) Et₂O

10: 96 percent / PCC / CH₂Cl₂

11: 23 percent / tetrahydrofuran / -78 °C

With diazomethane; pyridine; methanol; n-butyllithium; Phenylselenyl chloride; 18-crown-6 ether; dimethylsulfide; boron trifluoride diethyl etherate; dihydrogen peroxide; sodium hydride; potassium carbonate; lithium-n-butanethiolate; pyridinium chlorochromate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.3987/COM-90-5370