(5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone

Base Information

Chemical Name:(5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone
CAS No.:181705-70-4
Molecular Formula:C₃₀H₃₉NO₅Si
Molecular Weight:521.729
Hs Code.:

Synonyms:(5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone

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Chemical Property of (5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone

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Technology Process of (5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone

There total 10 articles about (5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone 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: 78.0%

: 121896-38-6
2-tert-butyldimethylsilyloxyfuran

: 782496-03-1
(2S,5S)-N-(tert-butoxycarbonyl)-5[(tert-butyldiphenylsilyl)oxymethyl]-2-methoxypyrrolidine

: 181705-70-4
(5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone

Guidance literature:: With t-butyldimethylsiyl triflate; In dichloromethane; at -80 ℃; for 1h;
DOI:10.1002/(SICI)1099-0690(199906)1999:6<1395::AID-EJOC1395>3.0.CO;2-T

Reference yield:

: 61550-02-5
(furan-2-yloxy)-trimethylsilane

: 192389-29-0
(2S,5S/R)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)methyl-5-methoxy-pyrrolidine

: 181705-70-4
(5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone

: (2S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((R)-5-oxo-2,5-dihydro-furan-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With boron trichloride-diethyl ether; at -78 ℃; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1016/S0960-894X(96)00275-2

Reference yield:

: 141293-28-9
N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole

: 181705-70-4
(5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone

Guidance literature:: Multi-step reaction with 9 steps

1: 78 percent / SnCl₄ / diethyl ether / 3 h / -80 °C

2: 90 percent / H₂; NaOAc / Pd/C / tetrahydrofuran / 24 h / 20 °C

3: AcOH; water / 8 h / 50 °C

4: NaIO₄ / CH₂Cl₂; H₂O / 0.25 h

5: 5.2 g / NaBH₄ / methanol / -30 - -15 °C

6: 83 percent / imidazole / dimethylformamide / 18 h / 20 °C

7: LiEt₃BH / tetrahydrofuran / 3 h / -78 °C

8: BF₃*OEt₂ / diethyl ether / 0.5 h / 20 °C

9: 78 percent / TBSOTf / CH₂Cl₂ / 1 h / -80 °C

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; water; hydrogen; sodium acetate; tin(IV) chloride; lithium triethylborohydride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 1: Mukaiyama aldolization / 2: Catalytic hydrogenation / 3: Hydrolysis / 4: Oxidation / 5: Reduction / 6: Substitution / 7: Reduction / 8: Alkylation / 9: Mannich reaction;
DOI:10.1002/(SICI)1099-0690(199906)1999:6<1395::AID-EJOC1395>3.0.CO;2-T