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

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Chemical Name:(S,2Z,4E)-allyl 2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienoate
CAS No.:935872-04-1
Molecular Formula:C₃₀H₄₅BrO₅Si
Molecular Weight:593.674
Hs Code.:

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

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

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

There total 10 articles about (S,2Z,4E)-allyl 2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienoate 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: 84.0%

: (allyloxycarbonylbromomethylidene)triphenylphosphorane

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

: 935872-04-1
(S,2Z,4E)-allyl 2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienoate

Guidance literature:: In benzene; at 70 ℃; for 39h;
DOI:10.1021/jo062089i

Reference yield:

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

: 935872-04-1
(S,2Z,4E)-allyl 2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienoate

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: 84 percent / benzene / 39 h / 70 °C

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

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 935872-04-1
(S,2Z,4E)-allyl 2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienoate

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: 84 percent / benzene / 39 h / 70 °C

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