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

Base Information

Chemical Name:(2'R,4R,5S)-3-(4'-benzyloxy-2'-hydroxybutylidene)-4-N-phenylaminodihydro-5-methylfuran-2-one
CAS No.:313963-39-2
Molecular Formula:C₂₂H₂₅NO₄
Molecular Weight:367.445
Hs Code.:

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

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

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

There total 10 articles about (2'R,4R,5S)-3-(4'-benzyloxy-2'-hydroxybutylidene)-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: 100.0%

: 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

: 313963-39-2
(2'R,4R,5S)-3-(4'-benzyloxy-2'-hydroxybutylidene)-4-N-phenylaminodihydro-5-methylfuran-2-one

Guidance literature:: With water; tris(acetonitrile)tricarbonylmolybdenum⁽⁰⁾; In acetonitrile; at 20 ℃; for 0.25h;
DOI:10.1002/anie.200462264

Reference yield:

: 5470-84-8
4-benzyloxybutanal

: 313963-39-2
(2'R,4R,5S)-3-(4'-benzyloxy-2'-hydroxybutylidene)-4-N-phenylaminodihydro-5-methylfuran-2-one

Guidance literature:: Multi-step reaction with 6 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

With 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; acetonitrile; 1.1: Wittig reaction / 2.1: Metallation / 2.2: Addition / 3.1: Cyclization / 4.1: Dehydration / 5.1: Cycloaddition / 6.1: Ring cleavage;
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

: 313963-39-2
(2'R,4R,5S)-3-(4'-benzyloxy-2'-hydroxybutylidene)-4-N-phenylaminodihydro-5-methylfuran-2-one

Guidance literature:: Multi-step reaction with 7 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

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