(2'R,4R,5S)-3-(4'-benzyloxy-2'-(tert-butyldimethylsilyloxy)butylidene)-4-N-phenylaminodihydro-5-methylfuran-2-one

Base Information

• Chemical Name: (2'R,4R,5S)-3-(4'-benzyloxy-2'-(tert-butyldimethylsilyloxy)butylidene)-4-N-phenylaminodihydro-5-methylfuran-2-one
• CAS No.: 313963-49-4
• Molecular Formula: C₂₈H₃₉NO₄Si
• Molecular Weight: 481.707

Synonyms:(2'R,4R,5S)-3-(4'-benzyloxy-2'-(tert-butyldimethylsilyloxy)butylidene)-4-N-phenylaminodihydro-5-methylfuran-2-one

Chemical Property of (2'R,4R,5S)-3-(4'-benzyloxy-2'-(tert-butyldimethylsilyloxy)butylidene)-4-N-phenylaminodihydro-5-methylfuran-2-one

Chemical Property:

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Technology Process of (2'R,4R,5S)-3-(4'-benzyloxy-2'-(tert-butyldimethylsilyloxy)butylidene)-4-N-phenylaminodihydro-5-methylfuran-2-one

There total 11 articles about (2'R,4R,5S)-3-(4'-benzyloxy-2'-(tert-butyldimethylsilyloxy)butylidene)-4-N-phenylaminodihydro-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: 83.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2'R,4R,5S)-3-(4'-benzyloxy-2'-hydroxybutylidene)-4-N-phenylaminodihydro-5-methylfuran-2-one (313963-39-2) → (2'R,4R,5S)-3-(4'-benzyloxy-2'-(tert-butyldimethylsilyloxy)butylidene)-4-N-phenylaminodihydro-5-methylfuran-2-one (313963-49-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 14h;

DOI:10.1002/1521-3765(20020402)8:7<1621::AID-CHEM1621>3.0.CO;2-8

Reference yield:

4-benzyloxybutanal (5470-84-8) → (2'R,4R,5S)-3-(4'-benzyloxy-2'-(tert-butyldimethylsilyloxy)butylidene)-4-N-phenylaminodihydro-5-methylfuran-2-one (313963-49-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: CH₂Cl₂ / 14 h / 0 - 20 °C

2.1: LDA; HMPA / tetrahydrofuran / 0.5 h / -78 °C

2.2: tetrahydrofuran / -78 - 0 °C

3.1: HCl / methanol / 0.08 h / 20 °C

4.1: MsCl; NEt₃ / CH₂Cl₂ / 0.5 h / 0 °C

5.1: I₂ / methanol; CH₂Cl₂ / 14 h / 0 °C / Irradiation

6.1: 70 percent / [Mo(CO)3(MeCN)3]; H₂O / acetonitrile / 0.25 h / 20 °C

7.1: 80 percent / imidazole / dimethylformamide / 14 h / 20 °C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; tris(acetonitrile)tricarbonylmolybdenum⁽⁰⁾; water; iodine; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Wittig reaction / 2.1: Metallation / 2.2: Addition / 3.1: Cyclization / 4.1: Dehydration / 5.1: Cycloaddition / 6.1: Ring cleavage / 7.1: Etherification;

DOI:10.1002/1521-3773(20001016)39:20<3622::AID-ANIE3622>3.0.CO;2-H

Reference yield:

4-benzyloxy-butan-1-ol (4541-14-4) → (2'R,4R,5S)-3-(4'-benzyloxy-2'-(tert-butyldimethylsilyloxy)butylidene)-4-N-phenylaminodihydro-5-methylfuran-2-one (313963-49-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: DMSO; (COCl)2; NEt₃ / CH₂Cl₂ / -78 - 0 °C

2.1: CH₂Cl₂ / 14 h / 0 - 20 °C

3.1: LDA; HMPA / tetrahydrofuran / 0.5 h / -78 °C

3.2: tetrahydrofuran / -78 - 0 °C

4.1: HCl / methanol / 0.08 h / 20 °C

5.1: MsCl; NEt₃ / CH₂Cl₂ / 0.5 h / 0 °C

6.1: I₂ / methanol; CH₂Cl₂ / 14 h / 0 °C / Irradiation

7.1: 70 percent / [Mo(CO)3(MeCN)3]; H₂O / acetonitrile / 0.25 h / 20 °C

8.1: 80 percent / imidazole / dimethylformamide / 14 h / 20 °C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; tris(acetonitrile)tricarbonylmolybdenum⁽⁰⁾; water; iodine; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Swern oxidation / 2.1: Wittig reaction / 3.1: Metallation / 3.2: Addition / 4.1: Cyclization / 5.1: Dehydration / 6.1: Cycloaddition / 7.1: Ring cleavage / 8.1: Etherification;

DOI:10.1002/1521-3773(20001016)39:20<3622::AID-ANIE3622>3.0.CO;2-H

upstream raw materials:

tert-butyldimethylsilyl chloride

(2'R,4R,5S)-3-(4'-benzyloxy-2'-hydroxybutylidene)-4-N-phenylaminodihydro-5-methylfuran-2-one

Nitrosobenzene

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

Downstream raw materials:

N-{4-[2-(tert-butyl-dimethyl-silanyloxy)-4-oxo-butyl]-2-methyl-5-oxo-tetrahydro-furan-3-yl}-2,2,2-trifluoro-N-phenyl-acetamide

(2'S,3R,4R,5S)-3-(4'-hydroxy-2'-tert-butyldimethylsilyloxy)butyl-4-N-phenyl-N-trifluoroacetamido-2,3,4,5-tetrahydro-5-methylfuran-2-one

(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

(2'S,3R,4R,5S)-3-(4'-benzyloxy-2'-tert-butyldimethylsilyloxy)butyl-4-N-phenyl-N-trifluoroacetamido-2,3,4,5-tetrahydro-5-methylfuran-2-one

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