phenyl (2S,3S,4R)-4-[(R)-5-[(tert-butyldimethylsilyl)oxy]-1-iodo-pent-1-yn-3-yl]-3,4-epoxy-2-iodoethynyl-3,4-dihydro-2H-quinoline-1-carboxylate

Base Information

Chemical Name:phenyl (2S,3S,4R)-4-[(R)-5-[(tert-butyldimethylsilyl)oxy]-1-iodo-pent-1-yn-3-yl]-3,4-epoxy-2-iodoethynyl-3,4-dihydro-2H-quinoline-1-carboxylate
CAS No.:718629-34-6
Molecular Formula:C₂₉H₃₁I₂NO₄Si
Molecular Weight:739.464
Hs Code.:

Synonyms:phenyl (2S,3S,4R)-4-[(R)-5-[(tert-butyldimethylsilyl)oxy]-1-iodo-pent-1-yn-3-yl]-3,4-epoxy-2-iodoethynyl-3,4-dihydro-2H-quinoline-1-carboxylate

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Chemical Property of phenyl (2S,3S,4R)-4-[(R)-5-[(tert-butyldimethylsilyl)oxy]-1-iodo-pent-1-yn-3-yl]-3,4-epoxy-2-iodoethynyl-3,4-dihydro-2H-quinoline-1-carboxylate

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Technology Process of phenyl (2S,3S,4R)-4-[(R)-5-[(tert-butyldimethylsilyl)oxy]-1-iodo-pent-1-yn-3-yl]-3,4-epoxy-2-iodoethynyl-3,4-dihydro-2H-quinoline-1-carboxylate

There total 12 articles about phenyl (2S,3S,4R)-4-[(R)-5-[(tert-butyldimethylsilyl)oxy]-1-iodo-pent-1-yn-3-yl]-3,4-epoxy-2-iodoethynyl-3,4-dihydro-2H-quinoline-1-carboxylate 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: 85.0%

: phenyl (2S,3S,4R)-4-[(R)-5-[(tert-butyldimethylsilyl)oxy]pent-1-yn-3-yl]-3,4-epoxy-2-ethynyl-3,4-dihydro-2H-quinoline-1-carboxylate

: 718629-34-6
phenyl (2S,3S,4R)-4-[(R)-5-[(tert-butyldimethylsilyl)oxy]-1-iodo-pent-1-yn-3-yl]-3,4-epoxy-2-iodoethynyl-3,4-dihydro-2H-quinoline-1-carboxylate

Guidance literature:: With morpholine-iodine complex; In benzene; at 20 ℃; for 46h;
DOI:10.1002/ejoc.200901478

Reference yield:

: 213478-44-5
(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-quinolin-4-yl-propan-1-ol

: 718629-34-6
phenyl (2S,3S,4R)-4-[(R)-5-[(tert-butyldimethylsilyl)oxy]-1-iodo-pent-1-yn-3-yl]-3,4-epoxy-2-iodoethynyl-3,4-dihydro-2H-quinoline-1-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

1.1: pyridine

2.1: nBu₄NI / dimethylsulfoxide

3.1: DIBAL-H / -70 °C

3.2: 62 percent / NaBH₄ / methanol / -40 - -10 °C

4.1: 100 percent / pyridine

5.1: tetrahydrofuran / -78 °C

6.1: HF / acetonitrile; H₂O / 0 °C

7.1: (COCl)2; EtN(iPr)2; DMSO / CH₂Cl₂ / 14 h / -78 °C

8.1: 77 percent / PPh₃ / CH₂Cl₂ / -78 - -40 °C

9.1: n-BuLi / -78 °C

9.2: 57 percent / K₂CO₃ / methanol / 0 °C

10.1: imidazole / dimethylformamide

11.1: MCPBA / CH₂Cl₂ / 20 °C

12.1: I₂*morpholine / benzene / 46 h / 20 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; iodine-morpholine complex; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; pyridine; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene; 7.1: Swern oxidation / 8.1: Corey-Fuchs reaction;
DOI:10.1016/j.tetlet.2004.04.029

Reference yield:

: 213478-42-3
Acetic acid (S)-3-hydroxy-2-quinolin-4-yl-propyl ester

: 718629-34-6
phenyl (2S,3S,4R)-4-[(R)-5-[(tert-butyldimethylsilyl)oxy]-1-iodo-pent-1-yn-3-yl]-3,4-epoxy-2-iodoethynyl-3,4-dihydro-2H-quinoline-1-carboxylate

Guidance literature:: Multi-step reaction with 14 steps

1.1: imidazole / dimethylformamide

2.1: KOH / methanol / 0 °C

3.1: pyridine

4.1: nBu₄NI / dimethylsulfoxide

5.1: DIBAL-H / -70 °C

5.2: 62 percent / NaBH₄ / methanol / -40 - -10 °C

6.1: 100 percent / pyridine

7.1: tetrahydrofuran / -78 °C

8.1: HF / acetonitrile; H₂O / 0 °C

9.1: (COCl)2; EtN(iPr)2; DMSO / CH₂Cl₂ / 14 h / -78 °C

10.1: 77 percent / PPh₃ / CH₂Cl₂ / -78 - -40 °C

11.1: n-BuLi / -78 °C

11.2: 57 percent / K₂CO₃ / methanol / 0 °C

12.1: imidazole / dimethylformamide

13.1: MCPBA / CH₂Cl₂ / 20 °C

14.1: I₂*morpholine / benzene / 46 h / 20 °C

With 1H-imidazole; potassium hydroxide; n-butyllithium; oxalyl dichloride; iodine-morpholine complex; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene; 9.1: Swern oxidation / 10.1: Corey-Fuchs reaction;
DOI:10.1016/j.tetlet.2004.04.029