(3R,4R,5R,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-3,4-dihydroxytetrahydrofuran-2-one

Base Information

Chemical Name:(3R,4R,5R,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-3,4-dihydroxytetrahydrofuran-2-one
CAS No.:244274-70-2
Molecular Formula:C₃₀H₄₁NO₇Si
Molecular Weight:555.744
Hs Code.:

Synonyms:(3R,4R,5R,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-3,4-dihydroxytetrahydrofuran-2-one

Suppliers and Price of (3R,4R,5R,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-3,4-dihydroxytetrahydrofuran-2-one

Supply Marketing:

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

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (3R,4R,5R,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-3,4-dihydroxytetrahydrofuran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (3R,4R,5R,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-3,4-dihydroxytetrahydrofuran-2-one

There total 10 articles about (3R,4R,5R,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-3,4-dihydroxytetrahydrofuran-2-one 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: 72.0%

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

: 244274-70-2
(3R,4R,5R,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-3,4-dihydroxytetrahydrofuran-2-one

Guidance literature:: With potassium permanganate; dicyclohexano-18-crown-6; In dichloromethane; for 4h;
DOI:10.1002/(SICI)1099-0690(199906)1999:6<1395::AID-EJOC1395>3.0.CO;2-T

Reference yield:

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

: 244274-70-2
(3R,4R,5R,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-3,4-dihydroxytetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 10 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

10: 72 percent / cis-dicyclohexano-18-crown-6 ether; KMnO₄ / CH₂Cl₂ / 4 h

With 1H-imidazole; sodium tetrahydroborate; potassium permanganate; sodium periodate; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; water; hydrogen; sodium acetate; dicyclohexano-18-crown-6; 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 / 10: Oxidation;
DOI:10.1002/(SICI)1099-0690(199906)1999:6<1395::AID-EJOC1395>3.0.CO;2-T

Reference yield:

: 141393-87-5
4-<(tert-butoxycarbonyl)amino>-6,7-O-isopropylidene-2,3,4-trideoxy-L-arabino-hept-2-enonic acid 1,4-lactam

: 244274-70-2
(3R,4R,5R,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-3,4-dihydroxytetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / H₂; NaOAc / Pd/C / tetrahydrofuran / 24 h / 20 °C

2: AcOH; water / 8 h / 50 °C

3: NaIO₄ / CH₂Cl₂; H₂O / 0.25 h

4: 5.2 g / NaBH₄ / methanol / -30 - -15 °C

5: 83 percent / imidazole / dimethylformamide / 18 h / 20 °C

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

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

8: 78 percent / TBSOTf / CH₂Cl₂ / 1 h / -80 °C

9: 72 percent / cis-dicyclohexano-18-crown-6 ether; KMnO₄ / CH₂Cl₂ / 4 h

With 1H-imidazole; sodium tetrahydroborate; potassium permanganate; sodium periodate; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; water; hydrogen; sodium acetate; dicyclohexano-18-crown-6; lithium triethylborohydride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 1: Catalytic hydrogenation / 2: Hydrolysis / 3: Oxidation / 4: Reduction / 5: Substitution / 6: Reduction / 7: Alkylation / 8: Mannich reaction / 9: Oxidation;
DOI:10.1002/(SICI)1099-0690(199906)1999:6<1395::AID-EJOC1395>3.0.CO;2-T