(+)-(S,2E,4E)-2-bromo-7-hydroxy-7-((1R,2R)-2-((4 methoxybenzyloxy)methyl)cyclopentyl)hepta-2,4-dienenitrile

Base Information

Chemical Name:(+)-(S,2E,4E)-2-bromo-7-hydroxy-7-((1R,2R)-2-((4 methoxybenzyloxy)methyl)cyclopentyl)hepta-2,4-dienenitrile
CAS No.:714974-03-5
Molecular Formula:C₂₁H₂₆BrNO₃
Molecular Weight:420.346
Hs Code.:

Synonyms:(+)-(S,2E,4E)-2-bromo-7-hydroxy-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-hydroxy-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-hydroxy-7-((1R,2R)-2-((4 methoxybenzyloxy)methyl)cyclopentyl)hepta-2,4-dienenitrile

There total 11 articles about (+)-(S,2E,4E)-2-bromo-7-hydroxy-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: 94.0%

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

: 714974-03-5
(+)-(S,2E,4E)-2-bromo-7-hydroxy-7-((1R,2R)-2-((4 methoxybenzyloxy)methyl)cyclopentyl)hepta-2,4-dienenitrile

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 48h;
DOI:10.1021/ol049356w

Reference yield: 93.0%

: 1259491-34-3
C₁₉H₂₆O₄

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

: 714974-03-5
(+)-(S,2E,4E)-2-bromo-7-hydroxy-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 4h;
DOI:10.1002/chem.201001284

Reference yield:

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

: 714974-03-5
(+)-(S,2E,4E)-2-bromo-7-hydroxy-7-((1R,2R)-2-((4 methoxybenzyloxy)methyl)cyclopentyl)hepta-2,4-dienenitrile

Guidance literature:: Multi-step reaction with 9 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

9: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; water; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 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