(S,2E,4E)-2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienenitrile

Base Information

Chemical Name:(S,2E,4E)-2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienenitrile
CAS No.:714974-17-1
Molecular Formula:C₂₇H₄₀BrNO₃Si
Molecular Weight:534.609
Hs Code.:

Synonyms:(S,2E,4E)-2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienenitrile

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Chemical Property of (S,2E,4E)-2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienenitrile

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Technology Process of (S,2E,4E)-2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienenitrile

There total 10 articles about (S,2E,4E)-2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienenitrile 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: 96.0%

: 155440-91-8
diethyl 1-bromo(1-cyanomethyl)phosphonate

: 714974-02-4
(1'R,2'R,5S)-5-(tert-butyldimethylsilyloxy)-5-[2'-(4''-methoxybenzyloxymethyl)cyclopentyl]penta-2E-enal

: 714974-17-1
(S,2E,4E)-2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienenitrile

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile; at 0 ℃; for 2h;
DOI:10.1021/ol049356w

Reference yield:

: 57287-24-8
(1R,2R)-1,2-(dihydroxymethyl)cyclopentane

: 714974-17-1
(S,2E,4E)-2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienenitrile

Guidance literature:: Multi-step reaction with 8 steps

1: NaH / dimethylformamide / -20 - 20 °C

2: 6.24 g / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

3: 54 percent / tetrahydrofuran / 0.5 h / -78 °C

4: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

5: H₂O; NMO; OsO₄ / acetone / 4 h / 20 °C

6: 533 mg / NaIO₄; H₂O / methanol / 2 h / 0 °C

7: 73 percent / benzene / 48 h / 80 °C

8: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; water; sodium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; benzene; 2: Dess-Martin oxidation / 7: Wittig reaction;
DOI:10.1021/jo062089i

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 714974-17-1
(S,2E,4E)-2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienenitrile

Guidance literature:: Multi-step reaction with 8 steps

1: NaH / dimethylformamide / -20 - 20 °C

2: 6.24 g / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

3: 54 percent / tetrahydrofuran / 0.5 h / -78 °C

4: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

5: H₂O; NMO; OsO₄ / acetone / 4 h / 20 °C

6: 533 mg / NaIO₄; H₂O / methanol / 2 h / 0 °C

7: 73 percent / benzene / 48 h / 80 °C

8: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; water; sodium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; benzene; 2: Dess-Martin oxidation / 7: Wittig reaction;
DOI:10.1021/jo062089i