(3S,6R,7R,8R,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8-tris-trimethylsilanyloxy-hexahydro-indolizin-5-one

Base Information

Chemical Name:(3S,6R,7R,8R,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8-tris-trimethylsilanyloxy-hexahydro-indolizin-5-one
CAS No.:244274-74-6
Molecular Formula:C₃₄H₅₇NO₅Si₄
Molecular Weight:672.172
Hs Code.:

Synonyms:(3S,6R,7R,8R,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8-tris-trimethylsilanyloxy-hexahydro-indolizin-5-one

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Chemical Property of (3S,6R,7R,8R,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8-tris-trimethylsilanyloxy-hexahydro-indolizin-5-one

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Technology Process of (3S,6R,7R,8R,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8-tris-trimethylsilanyloxy-hexahydro-indolizin-5-one

There total 11 articles about (3S,6R,7R,8R,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8-tris-trimethylsilanyloxy-hexahydro-indolizin-5-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: 94.0%

: 75-77-4
chloro-trimethyl-silane

: 244274-71-3
(3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one

: 244274-74-6
(3S,6R,7R,8R,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8-tris-trimethylsilanyloxy-hexahydro-indolizin-5-one

Guidance literature:: With pyridine; at 25 ℃; for 12h;
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

: 244274-74-6
(3S,6R,7R,8R,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8-tris-trimethylsilanyloxy-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 11 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

10: 84 percent / thiophenol; TMSOTf / CH₂Cl₂ / 1 h / 0 °C

11: 94 percent / pyridine / 12 h / 25 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; potassium permanganate; sodium periodate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; water; hydrogen; sodium acetate; dicyclohexano-18-crown-6; lithium triethylborohydride; acetic acid; thiophenol; 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 / 10: Decarboxylation / 11: Substitution;
DOI:10.1002/(SICI)1099-0690(199906)1999:6<1395::AID-EJOC1395>3.0.CO;2-T

Reference yield:

: 138629-30-8,138871-56-4
(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate

: 244274-74-6
(3S,6R,7R,8R,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8-tris-trimethylsilanyloxy-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 6 steps

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

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

3: 78 percent / TBSOTf / CH₂Cl₂ / 1 h / -80 °C

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

5: 84 percent / thiophenol; TMSOTf / CH₂Cl₂ / 1 h / 0 °C

6: 94 percent / pyridine / 12 h / 25 °C

With pyridine; potassium permanganate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; dicyclohexano-18-crown-6; lithium triethylborohydride; thiophenol; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Reduction / 2: Alkylation / 3: Mannich reaction / 4: Oxidation / 5: Decarboxylation / 6: Substitution;
DOI:10.1002/(SICI)1099-0690(199906)1999:6<1395::AID-EJOC1395>3.0.CO;2-T