(3S,6S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,8-dihydroxy-6-methyl-hexahydro-indolizin-5-one

Base Information

Chemical Name:(3S,6S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,8-dihydroxy-6-methyl-hexahydro-indolizin-5-one
CAS No.:267661-40-5
Molecular Formula:C₂₆H₃₅NO₄Si
Molecular Weight:453.654
Hs Code.:

Synonyms:(3S,6S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,8-dihydroxy-6-methyl-hexahydro-indolizin-5-one

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Chemical Property of (3S,6S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,8-dihydroxy-6-methyl-hexahydro-indolizin-5-one

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Technology Process of (3S,6S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,8-dihydroxy-6-methyl-hexahydro-indolizin-5-one

There total 7 articles about (3S,6S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,8-dihydroxy-6-methyl-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: 84.0%

: 267661-17-6
(3S,6S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6-hydroxy-8-(4-methoxy-benzyloxy)-6-methyl-hexahydro-indolizin-5-one

: 267661-40-5
(3S,6S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,8-dihydroxy-6-methyl-hexahydro-indolizin-5-one

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
DOI:10.1016/S0960-894X(99)00669-1

Reference yield:

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

: 267661-40-5
(3S,6S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,8-dihydroxy-6-methyl-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / H₂ / 10 percent Pd/C / ethyl acetate

2: 71 percent / B-bromocatecholborane / CH₂Cl₂

3: 98 percent / NaOMe / methanol

4: 86 percent / Bu₄NI / tetrahydrofuran

5: 97 percent / t-BuLi / tetrahydrofuran / -78 °C

6: 64 percent / t-BuLi; (MeO)3P; O₂ / tetrahydrofuran / -78 °C

7: 84 percent / DDQ / CH₂Cl₂; H₂O

With bromocatecholborane; hydrogen; tert.-butyl lithium; oxygen; sodium methylate; tetra-(n-butyl)ammonium iodide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; phosphorous acid trimethyl ester; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; 1: Catalytic hydrogenation / 2: Decarboxylation / 3: lactam formation / 4: Etherification / 5: Methylation / 6: hydroxylation / 7: deprotection;
DOI:10.1016/S0960-894X(99)00669-1

Reference yield:

: 181705-71-5
(5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one

: 267661-40-5
(3S,6S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,8-dihydroxy-6-methyl-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / NaOMe / methanol

2: 86 percent / Bu₄NI / tetrahydrofuran

3: 97 percent / t-BuLi / tetrahydrofuran / -78 °C

4: 64 percent / t-BuLi; (MeO)3P; O₂ / tetrahydrofuran / -78 °C

5: 84 percent / DDQ / CH₂Cl₂; H₂O

With tert.-butyl lithium; oxygen; sodium methylate; tetra-(n-butyl)ammonium iodide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; dichloromethane; water; 1: lactam formation / 2: Etherification / 3: Methylation / 4: hydroxylation / 5: deprotection;
DOI:10.1016/S0960-894X(99)00669-1