(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

Base Information

Chemical Name:(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
CAS No.:313963-41-6
Molecular Formula:C₃₀H₄₀F₃NO₅Si
Molecular Weight:579.732
Hs Code.:

Synonyms:(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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Chemical Property of (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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Technology Process of (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

There total 13 articles about (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 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: 95.0%

: 407-25-0
trifluoroacetic anhydride

: 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

: 313963-41-6
(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

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1002/1521-3765(20020402)8:7<1621::AID-CHEM1621>3.0.CO;2-8

Reference yield:

: 5470-84-8
4-benzyloxybutanal

: 313963-41-6
(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

Guidance literature:: Multi-step reaction with 9 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

8.1: 92 percent / H₂ / 20 mol percent PtO₂ / ethanol / 0.5 h / 20 °C

9.1: Huenig's base / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; tris(acetonitrile)tricarbonylmolybdenum⁽⁰⁾; water; hydrogen; iodine; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; 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 / 8.1: Catalytic hydrogenation / 9.1: Acylation;
DOI:10.1002/1521-3773(20001016)39:20<3622::AID-ANIE3622>3.0.CO;2-H

Reference yield:

: 4541-14-4
4-benzyloxy-butan-1-ol

: 313963-41-6
(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

Guidance literature:: Multi-step reaction with 10 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

9.1: 92 percent / H₂ / 20 mol percent PtO₂ / ethanol / 0.5 h / 20 °C

10.1: Huenig's base / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; tris(acetonitrile)tricarbonylmolybdenum⁽⁰⁾; water; hydrogen; iodine; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; 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 / 9.1: Catalytic hydrogenation / 10.1: Acylation;
DOI:10.1002/1521-3773(20001016)39:20<3622::AID-ANIE3622>3.0.CO;2-H