(3S,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-5-one

Base Information

Chemical Name:(3S,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-5-one
CAS No.:244274-69-9
Molecular Formula:C₃₁H₄₇NO₃Si₂
Molecular Weight:537.89
Hs Code.:

Synonyms:(3S,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-5-one

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Chemical Property of (3S,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-5-one

Chemical Property:

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Technology Process of (3S,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-5-one

There total 12 articles about (3S,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-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: 96.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 181705-72-6
(3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-hydroxyhexahydroindolizin-5-one

: 244274-69-9
(3S,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-5-one

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 36h;
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

: 244274-69-9
(3S,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-5-one

Guidance literature:: Multi-step reaction with 7 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: 90 percent / H₂; AcONa / Pd/C / tetrahydrofuran / 24 h / 20 °C

5: 88 percent / thiophenol; TMSOTf / CH₂Cl₂ / 1 h / 0 °C

6: 69 percent / NaOMe / methanol / 1 h / 0 °C

7: 96 percent / imidazole / dimethylformamide / 36 h / 20 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; hydrogen; sodium methylate; sodium acetate; lithium triethylborohydride; thiophenol; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: Alkylation / 3: Mannich reaction / 4: Catalytic hydrogenation / 5: Decarboxylation / 6: Rearrangement / 7: Substitution;
DOI:10.1002/(SICI)1099-0690(199906)1999:6<1395::AID-EJOC1395>3.0.CO;2-T

Reference yield:

: 81658-25-5,344884-10-2
2-hydroxymethyl-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester

: 244274-69-9
(3S,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-5-one

Guidance literature:: Multi-step reaction with 8 steps

1: 83 percent / imidazole / dimethylformamide / 18 h / 20 °C

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

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

4: 78 percent / TBSOTf / CH₂Cl₂ / 1 h / -80 °C

5: 90 percent / H₂; AcONa / Pd/C / tetrahydrofuran / 24 h / 20 °C

6: 88 percent / thiophenol; TMSOTf / CH₂Cl₂ / 1 h / 0 °C

7: 69 percent / NaOMe / methanol / 1 h / 0 °C

8: 96 percent / imidazole / dimethylformamide / 36 h / 20 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; hydrogen; sodium methylate; sodium acetate; lithium triethylborohydride; thiophenol; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Reduction / 3: Alkylation / 4: Mannich reaction / 5: Catalytic hydrogenation / 6: Decarboxylation / 7: Rearrangement / 8: Substitution;
DOI:10.1002/(SICI)1099-0690(199906)1999:6<1395::AID-EJOC1395>3.0.CO;2-T