(+)-(3R,5R)-1-fluoro-3-(O-tert-butyldimethylsilyloxymethyl)-5-O-benzyloxycyclopent-1-ene

Base Information

Chemical Name:(+)-(3R,5R)-1-fluoro-3-(O-tert-butyldimethylsilyloxymethyl)-5-O-benzyloxycyclopent-1-ene
CAS No.:855662-78-1
Molecular Formula:C₁₉H₂₉FO₂Si
Molecular Weight:336.522
Hs Code.:

Synonyms:(+)-(3R,5R)-1-fluoro-3-(O-tert-butyldimethylsilyloxymethyl)-5-O-benzyloxycyclopent-1-ene

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+)-(3R,5R)-1-fluoro-3-(O-tert-butyldimethylsilyloxymethyl)-5-O-benzyloxycyclopent-1-ene

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Technology Process of (+)-(3R,5R)-1-fluoro-3-(O-tert-butyldimethylsilyloxymethyl)-5-O-benzyloxycyclopent-1-ene

There total 9 articles about (+)-(3R,5R)-1-fluoro-3-(O-tert-butyldimethylsilyloxymethyl)-5-O-benzyloxycyclopent-1-ene 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: 83.0%

: 855662-75-8
(+)-(3R,5R)-1-fluoro-3-hydroxymethyl-5-O-benzyloxycyclopent-1-ene

: 18162-48-6
tert-butyldimethylsilyl chloride

: 855662-78-1
(+)-(3R,5R)-1-fluoro-3-(O-tert-butyldimethylsilyloxymethyl)-5-O-benzyloxycyclopent-1-ene

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃;
DOI:10.1021/jm050096d

Reference yield:

: 855662-67-8
(+)-(1R,2S,3S,4R)-1-O-benzyloxy-2,3-anhydro-4-hydroxymethylcyclopentane

: 855662-78-1
(+)-(3R,5R)-1-fluoro-3-(O-tert-butyldimethylsilyloxymethyl)-5-O-benzyloxycyclopent-1-ene

Guidance literature:: Multi-step reaction with 7 steps

1: 72 percent / LiAlH₄ / tetrahydrofuran / 20 °C

2: 83 percent / pyridine / Heating

3: 72 percent / pyridinium dichromate; AcOH; 4A molecular sieves / CH₂Cl₂ / 20 °C

4: 85 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / 20 °C

5: 95 percent / t-BuOK / tetrahydrofuran / 50 °C

6: 89 percent / aq. HCl / tetrahydrofuran; methanol / 50 °C

7: 83 percent / imidazole / CH₂Cl₂ / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; dipyridinium dichromate; diethylamino-sulfur trifluoride; 4 A molecular sieve; potassium tert-butylate; acetic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jm050096d

Reference yield:

: 855662-68-9
(+)-(1R,2S,4R)-1-O-benzyloxy-2-hydroxyl-4-hydroxymethylcyclopentane

: 855662-78-1
(+)-(3R,5R)-1-fluoro-3-(O-tert-butyldimethylsilyloxymethyl)-5-O-benzyloxycyclopent-1-ene

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / pyridine / Heating

2: 72 percent / pyridinium dichromate; AcOH; 4A molecular sieves / CH₂Cl₂ / 20 °C

3: 85 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / 20 °C

4: 95 percent / t-BuOK / tetrahydrofuran / 50 °C

5: 89 percent / aq. HCl / tetrahydrofuran; methanol / 50 °C

6: 83 percent / imidazole / CH₂Cl₂ / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; dipyridinium dichromate; diethylamino-sulfur trifluoride; 4 A molecular sieve; potassium tert-butylate; acetic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jm050096d