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

Base Information

Chemical Name:(1aR,3aS,4R,5R,5aR,8aR)-4-allyl-5-(4-((triisopropylsilyl)oxy)butyl)-2-oxodecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester
CAS No.:171523-53-8
Molecular Formula:C₃₄H₅₃NO₅Si
Molecular Weight:583.884
Hs Code.:

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

Suppliers and Price of (1aR,3aS,4R,5R,5aR,8aR)-4-allyl-5-(4-((triisopropylsilyl)oxy)butyl)-2-oxodecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester

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

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

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

There total 15 articles about (1aR,3aS,4R,5R,5aR,8aR)-4-allyl-5-(4-((triisopropylsilyl)oxy)butyl)-2-oxodecahydro-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: 90.0%

: 24850-33-7
allyltributylstanane

: 171523-60-7
(1aR,3aR,4R,5S,5aS,8aR)-5-(4-((triisopropylsilyl)oxy)butyl)-4-iodo-2-oxodecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester

: 171523-53-8
(1aR,3aS,4R,5R,5aR,8aR)-4-allyl-5-(4-((triisopropylsilyl)oxy)butyl)-2-oxodecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester

Guidance literature:: With 2,2'-azobis(isobutyronitrile); at 80 ℃; for 12h;
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

: 171523-53-8
(1aR,3aS,4R,5R,5aR,8aR)-4-allyl-5-(4-((triisopropylsilyl)oxy)butyl)-2-oxodecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 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

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

Reference yield:

: 144534-49-6
(2S,3aR,7aR)-3a-hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 171523-53-8
(1aR,3aS,4R,5R,5aR,8aR)-4-allyl-5-(4-((triisopropylsilyl)oxy)butyl)-2-oxodecahydro-3-oxa-6-aza-as-indacene-6-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 90 percent / DMAP, pyridine / CH₂Cl₂ / 24 h / Heating

2: 99 percent / NaBH₄, CeCl₃*7H₂O / diisopropyl ether; methanol / 2 h / 0 °C

3: 1.) tris(dibenzylideneacetone)dipalladium⁽⁰⁾*CHCl₃, tri-n-butylphosphine, HCO₂H, Et₃N, 2.) tetrapropylammonium perruthenate, N-methylmorpholine N-oxide monohydrate / 1.) THF, 60 deg C, 7 h, 2.) CH₂Cl₂, from 0 deg to RT, 4 h

4: 34 percent / potassium hexamethyldisilazane / tetrahydrofuran / 3 h / -60 °C

5: 91 percent / NaBH₄, CeCl₃*7H₂O / tetrahydrofuran; methanol / 1.5 h / 40 °C

6: 85 percent / xylene / 8 h / Heating

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

8: 93 percent / NaBH₄ / tetrahydrofuran; methanol / 12 h

9: 100 percent / imidazole, (dimethylamino)pyridine / CH₂Cl₂ / 5 h / Ambient temperature

10: 90 percent / aq. LiOH*H₂O / tetrahydrofuran; methanol / 24 h / 40 °C

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

12: Et₃N / 1 h / 0 - 22 °C

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

14: 85 percent / I₂, phosphate buffer / tetrahydrofuran / 2 h / 21 °C / pH 5.5

15: 90 percent / AIBN / 12 h / 80 °C

With pyridine; 1H-imidazole; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium hydroxide; sodium tetrahydroborate; sodium periodate; formic acid; phosphate buffer; cerium(III) chloride; tetrapropylammonium perruthennate; potassium hexamethyldisilazane; 2,2'-azobis(isobutyronitrile); tributylphosphine; iodine; tri-n-butyl-tin hydride; 4-methylmorpholine N-oxide; O-phenyl phosphorodichloridate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; In tetrahydrofuran; methanol; dichloromethane; di-isopropyl ether; xylene;
DOI:10.1021/ja00150a010