(E)-(2'S,3R,4R,5S)-3-(5'-iodo-2'-tert-butyldimethylsilyloxy)pent-4'-enyl-N-phenyl-N-trifluoroacetamido-2,3,4,5-tetrahydro-5-methylfuran-2-one

Base Information

Chemical Name:(E)-(2'S,3R,4R,5S)-3-(5'-iodo-2'-tert-butyldimethylsilyloxy)pent-4'-enyl-N-phenyl-N-trifluoroacetamido-2,3,4,5-tetrahydro-5-methylfuran-2-one
CAS No.:313963-42-7
Molecular Formula:C₂₄H₃₃F₃INO₄Si
Molecular Weight:611.516
Hs Code.:

Synonyms:(E)-(2'S,3R,4R,5S)-3-(5'-iodo-2'-tert-butyldimethylsilyloxy)pent-4'-enyl-N-phenyl-N-trifluoroacetamido-2,3,4,5-tetrahydro-5-methylfuran-2-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (E)-(2'S,3R,4R,5S)-3-(5'-iodo-2'-tert-butyldimethylsilyloxy)pent-4'-enyl-N-phenyl-N-trifluoroacetamido-2,3,4,5-tetrahydro-5-methylfuran-2-one

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (E)-(2'S,3R,4R,5S)-3-(5'-iodo-2'-tert-butyldimethylsilyloxy)pent-4'-enyl-N-phenyl-N-trifluoroacetamido-2,3,4,5-tetrahydro-5-methylfuran-2-one

There total 14 articles about (E)-(2'S,3R,4R,5S)-3-(5'-iodo-2'-tert-butyldimethylsilyloxy)pent-4'-enyl-N-phenyl-N-trifluoroacetamido-2,3,4,5-tetrahydro-5-methylfuran-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:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 313963-42-7
(E)-(2'S,3R,4R,5S)-3-(5'-iodo-2'-tert-butyldimethylsilyloxy)pent-4'-enyl-N-phenyl-N-trifluoroacetamido-2,3,4,5-tetrahydro-5-methylfuran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / imidazole / dimethylformamide / 14 h / 20 °C

2: 98 percent / H₂ / PtO₂ / methanol / 1.5 h / 20 °C

3: 95 percent / Huenig's base / CH₂Cl₂ / 0.5 h / 0 °C

4: 95 percent / H₂ / Pd(OH)2 / methanol / 48 h / 20 °C

5: 96 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.25 h / -78 - 20 °C

6: chromium dichloride / tetrahydrofuran / 14 h / 0 - 20 °C

With 1H-imidazole; chromium dichloride; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; platinum(IV) oxide; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5: Swern oxidation;
DOI:10.1002/1521-3765(20020402)8:7<1621::AID-CHEM1621>3.0.CO;2-8

Reference yield:

: 313963-38-1
(3S,6R,9R)-6-(2'-benzyloxy)-ethyl-3-methyl-4-phenyl-1,3,4,5,6,9-hexahydro-4-aza-5-oxoisobenzofuran-1-one

: 313963-42-7
(E)-(2'S,3R,4R,5S)-3-(5'-iodo-2'-tert-butyldimethylsilyloxy)pent-4'-enyl-N-phenyl-N-trifluoroacetamido-2,3,4,5-tetrahydro-5-methylfuran-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: [Mo(CO)3(MeCN)3] / acetonitrile / 0.25 h / 20 °C

1.2: 70 percent / H₂O / acetonitrile / 0.75 h / 20 °C

2.1: 83 percent / imidazole / dimethylformamide / 14 h / 20 °C

3.1: 98 percent / H₂ / PtO₂ / methanol / 1.5 h / 20 °C

4.1: 95 percent / Huenig's base / CH₂Cl₂ / 0.5 h / 0 °C

5.1: 95 percent / H₂ / Pd(OH)2 / methanol / 48 h / 20 °C

6.1: 96 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.25 h / -78 - 20 °C

7.1: chromium dichloride / tetrahydrofuran / 14 h / 0 - 20 °C

With 1H-imidazole; chromium dichloride; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; platinum(IV) oxide; palladium dihydroxide; tris(acetonitrile)tricarbonylmolybdenum⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 6.1: Swern oxidation;
DOI:10.1002/1521-3765(20020402)8:7<1621::AID-CHEM1621>3.0.CO;2-8

Reference yield:

: 313963-40-5
(2'S,3R,4R,5S)-3-(4'-benzyloxy-2'-tert-butyldimethylsilyloxy)butyl-4-N-phenylamino-2,3,4,5-tetrahydro-5-methylfuran-2-one

: 313963-42-7
(E)-(2'S,3R,4R,5S)-3-(5'-iodo-2'-tert-butyldimethylsilyloxy)pent-4'-enyl-N-phenyl-N-trifluoroacetamido-2,3,4,5-tetrahydro-5-methylfuran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / Huenig's base / CH₂Cl₂ / 0.5 h / 0 °C

2: 95 percent / H₂ / Pd(OH)2 / methanol / 48 h / 20 °C

3: 96 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.25 h / -78 - 20 °C

4: chromium dichloride / tetrahydrofuran / 14 h / 0 - 20 °C

With chromium dichloride; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; 3: Swern oxidation;
DOI:10.1002/1521-3765(20020402)8:7<1621::AID-CHEM1621>3.0.CO;2-8