(1aR,1S,3aS,4R,5R,5aR,8aR)-5-(4-((triisopropylsilyl)oxy)butyl)-1-methyl-2-oxo-4-vinyldecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester

Base Information

Chemical Name:(1aR,1S,3aS,4R,5R,5aR,8aR)-5-(4-((triisopropylsilyl)oxy)butyl)-1-methyl-2-oxo-4-vinyldecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester
CAS No.:171523-54-9
Molecular Formula:C₃₄H₅₃NO₅Si
Molecular Weight:583.884
Hs Code.:

(1aR,1S,3aS,4R,5R,5aR,8aR)-5-(4-((triisopropylsilyl)oxy)butyl)-1-methyl-2-oxo-4-vinyldecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester

Synonyms:(1aR,1S,3aS,4R,5R,5aR,8aR)-5-(4-((triisopropylsilyl)oxy)butyl)-1-methyl-2-oxo-4-vinyldecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester

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Chemical Property of (1aR,1S,3aS,4R,5R,5aR,8aR)-5-(4-((triisopropylsilyl)oxy)butyl)-1-methyl-2-oxo-4-vinyldecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester

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Technology Process of (1aR,1S,3aS,4R,5R,5aR,8aR)-5-(4-((triisopropylsilyl)oxy)butyl)-1-methyl-2-oxo-4-vinyldecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester

There total 20 articles about (1aR,1S,3aS,4R,5R,5aR,8aR)-5-(4-((triisopropylsilyl)oxy)butyl)-1-methyl-2-oxo-4-vinyldecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester 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:

: (1S,3aS,4R,5R,5aR,8aR,8bS)-1-Methyl-4-[2-(2-nitro-phenylselanyl)-ethyl]-2-oxo-5-(4-triisopropylsilanyloxy-butyl)-decahydro-furo[3,2-e]indole-6-carboxylic acid benzyl ester

: 171523-54-9
(1aR,1S,3aS,4R,5R,5aR,8aR)-5-(4-((triisopropylsilyl)oxy)butyl)-1-methyl-2-oxo-4-vinyldecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester

Guidance literature:: With dihydrogen peroxide; In tetrahydrofuran; at 21 ℃; for 6h; Yield given;
DOI:10.1021/ja00150a010

Reference yield:

: 171523-56-1
(2S,3aR,7aR)-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 171523-54-9
(1aR,1S,3aS,4R,5R,5aR,8aR)-5-(4-((triisopropylsilyl)oxy)butyl)-1-methyl-2-oxo-4-vinyldecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 17 steps

1: 34 percent / potassium hexamethyldisilazane / tetrahydrofuran / 3 h / -60 °C

2: 91 percent / NaBH₄, CeCl₃*7H₂O / tetrahydrofuran; methanol / 1.5 h / 40 °C

3: 85 percent / xylene / 8 h / Heating

4: 1.) AD-mix β, 2.) NaIO4 / 1.) T-BuOH, H2O, 5 deg C, 36 h, 2.) t-BuOH, H2O, RT, 45 min

5: 93 percent / NaBH₄ / tetrahydrofuran; methanol / 12 h

6: 100 percent / imidazole, (dimethylamino)pyridine / CH₂Cl₂ / 5 h / Ambient temperature

7: 90 percent / aq. LiOH*H₂O / tetrahydrofuran; methanol / 24 h / 40 °C

8: PhOPOCl₂, NEt₃ / tetrahydrofuran / 0.67 h / 0 - 22 °C

9: Et₃N / 1 h / 0 - 22 °C

10: Bu₃SnH, AIBN / xylene / 1 h / 130 °C

11: 85 percent / I₂, phosphate buffer / tetrahydrofuran / 2 h / 21 °C / pH 5.5

12: 90 percent / AIBN / 12 h / 80 °C

13: 1.) LDA, HMPA / 1.) tHF, hexane, -78 deg C, 30 min, 2.) THF, hexane, 20 min

14: OsO₄, NaIO₄ / tetrahydrofuran; H₂O / 1 h / 21 °C

15: NaBH₄ / tetrahydrofuran; methanol / 0.5 h / -40 °C

16: n-Bu₃P / tetrahydrofuran / 0.17 h / 0 °C

17: 30percent aq. H₂O₂ / tetrahydrofuran / 6 h / 21 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; phosphate buffer; cerium(III) chloride; potassium hexamethyldisilazane; 2,2'-azobis(isobutyronitrile); tributylphosphine; dihydrogen peroxide; iodine; tri-n-butyl-tin hydride; O-phenyl phosphorodichloridate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; xylene;
DOI:10.1021/ja00150a010

Reference yield:

: 171523-57-2
(2S,3aR,6R,7S,7aS)-6-hydroxy-7-pent-4-enyl-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 171523-54-9
(1aR,1S,3aS,4R,5R,5aR,8aR)-5-(4-((triisopropylsilyl)oxy)butyl)-1-methyl-2-oxo-4-vinyldecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 85 percent / xylene / 8 h / Heating

2: 1.) AD-mix β, 2.) NaIO4 / 1.) T-BuOH, H2O, 5 deg C, 36 h, 2.) t-BuOH, H2O, RT, 45 min

3: 93 percent / NaBH₄ / tetrahydrofuran; methanol / 12 h

4: 100 percent / imidazole, (dimethylamino)pyridine / CH₂Cl₂ / 5 h / Ambient temperature

5: 90 percent / aq. LiOH*H₂O / tetrahydrofuran; methanol / 24 h / 40 °C

6: PhOPOCl₂, NEt₃ / tetrahydrofuran / 0.67 h / 0 - 22 °C

7: Et₃N / 1 h / 0 - 22 °C

8: Bu₃SnH, AIBN / xylene / 1 h / 130 °C

9: 85 percent / I₂, phosphate buffer / tetrahydrofuran / 2 h / 21 °C / pH 5.5

10: 90 percent / AIBN / 12 h / 80 °C

11: 1.) LDA, HMPA / 1.) tHF, hexane, -78 deg C, 30 min, 2.) THF, hexane, 20 min

12: OsO₄, NaIO₄ / tetrahydrofuran; H₂O / 1 h / 21 °C

13: NaBH₄ / tetrahydrofuran; methanol / 0.5 h / -40 °C

14: n-Bu₃P / tetrahydrofuran / 0.17 h / 0 °C

15: 30percent aq. H₂O₂ / tetrahydrofuran / 6 h / 21 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; phosphate buffer; 2,2'-azobis(isobutyronitrile); tributylphosphine; dihydrogen peroxide; iodine; tri-n-butyl-tin hydride; O-phenyl phosphorodichloridate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; xylene;
DOI:10.1021/ja00150a010