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

Base Information

Chemical Name:(1'R,2'R,5S)-5-(tert-butyldimethylsilyloxy)-5-[2'-(4''-methoxybenzyloxymethyl)cyclopentyl]penta-2E-enal
CAS No.:714974-02-4
Molecular Formula:C₂₅H₄₀O₄Si
Molecular Weight:432.676
Hs Code.:

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

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Chemical Property of (1'R,2'R,5S)-5-(tert-butyldimethylsilyloxy)-5-[2'-(4''-methoxybenzyloxymethyl)cyclopentyl]penta-2E-enal

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Technology Process of (1'R,2'R,5S)-5-(tert-butyldimethylsilyloxy)-5-[2'-(4''-methoxybenzyloxymethyl)cyclopentyl]penta-2E-enal

There total 9 articles about (1'R,2'R,5S)-5-(tert-butyldimethylsilyloxy)-5-[2'-(4''-methoxybenzyloxymethyl)cyclopentyl]penta-2E-enal 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: 73.0%

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 714974-16-0
(1'R,2'R,3S)-3-(tert-butyldimethylsilyloxy)-3-[2'-(4''-methoxybenzyloxymethyl)cyclopentyl]propanal

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

Guidance literature:: In benzene; at 80 ℃; for 48h;
DOI:10.1021/ol049356w DOI:10.1021/jo062089i

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

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;
DOI:10.1021/jo062089i

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

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

Guidance literature:: Multi-step reaction with 7 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

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;
DOI:10.1021/jo062089i