(3S,3aS,4S,6S,7S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-((S)-2-hydroxy-1-methyl-ethyl)-3,6-dimethyl-6-[2-(2-nitro-phenylselanyl)-ethyl]-hexahydro-benzofuran-2-one

Base Information

Chemical Name:(3S,3aS,4S,6S,7S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-((S)-2-hydroxy-1-methyl-ethyl)-3,6-dimethyl-6-[2-(2-nitro-phenylselanyl)-ethyl]-hexahydro-benzofuran-2-one
CAS No.:86948-63-2
Molecular Formula:C₂₇H₄₃NO₆SeSi
Molecular Weight:584.687
Hs Code.:

(3S,3aS,4S,6S,7S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-((S)-2-hydroxy-1-methyl-ethyl)-3,6-dimethyl-6-[2-(2-nitro-phenylselanyl)-ethyl]-hexahydro-benzofuran-2-one

Synonyms:(3S,3aS,4S,6S,7S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-((S)-2-hydroxy-1-methyl-ethyl)-3,6-dimethyl-6-[2-(2-nitro-phenylselanyl)-ethyl]-hexahydro-benzofuran-2-one

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Chemical Property of (3S,3aS,4S,6S,7S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-((S)-2-hydroxy-1-methyl-ethyl)-3,6-dimethyl-6-[2-(2-nitro-phenylselanyl)-ethyl]-hexahydro-benzofuran-2-one

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Technology Process of (3S,3aS,4S,6S,7S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-((S)-2-hydroxy-1-methyl-ethyl)-3,6-dimethyl-6-[2-(2-nitro-phenylselanyl)-ethyl]-hexahydro-benzofuran-2-one

There total 6 articles about (3S,3aS,4S,6S,7S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-((S)-2-hydroxy-1-methyl-ethyl)-3,6-dimethyl-6-[2-(2-nitro-phenylselanyl)-ethyl]-hexahydro-benzofuran-2-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: 79.0%

: 51694-22-5
ortho-nitrophenyl selenocyanate

: 86992-99-6
8α-t-butyldimethylsilyloxy-2,3-dihydroxy-5,7αH,6,11βH-eleman-6,12-olide

: 86948-63-2
(3S,3aS,4S,6S,7S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-((S)-2-hydroxy-1-methyl-ethyl)-3,6-dimethyl-6-[2-(2-nitro-phenylselanyl)-ethyl]-hexahydro-benzofuran-2-one

: 86948-62-1
8α-t-butyldimethylsilyloxy-2,3-di-o-nitrophenylseleno-5,7-αH,6,11βH-eleman-6,12-olide

Guidance literature:: With tributylphosphine; In tetrahydrofuran; for 6h; Ambient temperature;
DOI:10.1016/S0040-4020(01)91278-5

Reference yield: 79.0%

: (2-nitrophenyl)seleno cyanate

: 86992-99-6
8α-t-butyldimethylsilyloxy-2,3-dihydroxy-5,7αH,6,11βH-eleman-6,12-olide

: 86948-63-2
(3S,3aS,4S,6S,7S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-((S)-2-hydroxy-1-methyl-ethyl)-3,6-dimethyl-6-[2-(2-nitro-phenylselanyl)-ethyl]-hexahydro-benzofuran-2-one

: 86948-62-1
8α-t-butyldimethylsilyloxy-2,3-di-o-nitrophenylseleno-5,7-αH,6,11βH-eleman-6,12-olide

Guidance literature:: With tributylphosphine; In tetrahydrofuran; for 6h; Ambient temperature;
DOI:10.1016/S0040-4039(00)81759-1

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 86948-63-2
(3S,3aS,4S,6S,7S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-((S)-2-hydroxy-1-methyl-ethyl)-3,6-dimethyl-6-[2-(2-nitro-phenylselanyl)-ethyl]-hexahydro-benzofuran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) H₂, 2.) imidazole / 1.) 5percent Pd-C / 1.) acetone, 2.) DMF, 30-40 deg C, 3.5 h

2: 1.) p-toluenesulphonylhydrazine, BF₃*Et₂O, 2.) LDA / 1.) benzene, 30 deg C, 3 h, 2.) THF/hexane, -78 deg C, then 0 deg C, 2 h

3: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, ethanol, -78 deg C, 15 min, 2.) -78 deg C, 45 min, then RT

4: 13 percent / n-Bu₃P / tetrahydrofuran / 6 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; tributylphosphine; boron trifluoride diethyl etherate; hydrogen; ozone; toluene-4-sulfonic acid hydrazide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran;
DOI:10.1016/S0040-4020(01)91278-5