(E)-(R)-8-[(4S,5R)-5-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-[1,3]dioxolan-2-yl-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester

Base Information

Chemical Name:(E)-(R)-8-[(4S,5R)-5-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-[1,3]dioxolan-2-yl-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester
CAS No.:543725-06-0
Molecular Formula:C₄₂H₅₂O₆Si
Molecular Weight:680.957
Hs Code.:

Synonyms:(E)-(R)-8-[(4S,5R)-5-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-[1,3]dioxolan-2-yl-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester

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Chemical Property of (E)-(R)-8-[(4S,5R)-5-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-[1,3]dioxolan-2-yl-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester

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Technology Process of (E)-(R)-8-[(4S,5R)-5-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-[1,3]dioxolan-2-yl-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester

There total 10 articles about (E)-(R)-8-[(4S,5R)-5-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-[1,3]dioxolan-2-yl-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-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:

: 1067-74-9
Methyl diethylphosphonoacetate

: 543725-26-4
(R)-6-[(4S,5R)-5-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-[1,3]dioxolan-2-yl-cyclohex-2-en-(E)-ylidene]-2-methyl-hexanal

: 543725-06-0
(E)-(R)-8-[(4S,5R)-5-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-[1,3]dioxolan-2-yl-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester

Guidance literature:: Methyl diethylphosphonoacetate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1.25h;

(R)-6-[(4S,5R)-5-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-[1,3]dioxolan-2-yl-cyclohex-2-en-(E)-ylidene]-2-methyl-hexanal; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1139/v02-196

Reference yield:

: 543724-84-1
(4S,5R)-5-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-cyclohex-2-enone

: 543725-06-0
(E)-(R)-8-[(4S,5R)-5-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-[1,3]dioxolan-2-yl-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: Br₂ / CCl₄ / 1.75 h / 0 °C

2.1: 9.27 g / Et₃N / CCl₄ / 0.67 h

3.1: n-BuLi / tetrahydrofuran / 2.5 h / 0 °C

3.2: CeCl₃ / tetrahydrofuran / 5 h / -78 °C

4.1: 8.77 g / tetrahydrofuran / -78 - 20 °C

5.1: t-BuLi / diethyl ether / -78 - 0 °C

5.2: CuCN / diethyl ether; tetrahydrofuran / 1 h / -68 °C

5.3: 96 percent / diethyl ether; tetrahydrofuran / 3 h / -50 - 0 °C

6.1: n-BuLi / tetrahydrofuran / 0.33 h / -78 °C

6.2: 80 percent / tetrahydrofuran / 1 h / -78 °C

7.1: 95 percent / PPTS / benzene / 6 h / Heating

8.1: 58 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

9.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

10.1: NaH / tetrahydrofuran / 1.25 h / 0 °C

10.2: 1.34 g / tetrahydrofuran / 0.5 h / 0 °C

With n-butyllithium; tetrabutyl ammonium fluoride; bromine; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; tetrachloromethane; diethyl ether; dichloromethane; benzene;
DOI:10.1139/v02-196

Reference yield:

: 543724-87-4
(4S,5R)-5-Benzyloxy-2-bromo-4-(tert-butyl-diphenyl-silanyloxy)-cyclohex-2-enone

: 543725-06-0
(E)-(R)-8-[(4S,5R)-5-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-[1,3]dioxolan-2-yl-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran / 2.5 h / 0 °C

1.2: CeCl₃ / tetrahydrofuran / 5 h / -78 °C

2.1: 8.77 g / tetrahydrofuran / -78 - 20 °C

3.1: t-BuLi / diethyl ether / -78 - 0 °C

3.2: CuCN / diethyl ether; tetrahydrofuran / 1 h / -68 °C

3.3: 96 percent / diethyl ether; tetrahydrofuran / 3 h / -50 - 0 °C

4.1: n-BuLi / tetrahydrofuran / 0.33 h / -78 °C

4.2: 80 percent / tetrahydrofuran / 1 h / -78 °C

5.1: 95 percent / PPTS / benzene / 6 h / Heating

6.1: 58 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

8.1: NaH / tetrahydrofuran / 1.25 h / 0 °C

8.2: 1.34 g / tetrahydrofuran / 0.5 h / 0 °C

With n-butyllithium; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1139/v02-196