(4S,5R)-5-Dibenzylamino-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-methylene-pentanoic acid ethyl ester

Base Information

Chemical Name:(4S,5R)-5-Dibenzylamino-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-methylene-pentanoic acid ethyl ester
CAS No.:205489-06-1
Molecular Formula:C₂₇H₃₅NO₅
Molecular Weight:453.579
Hs Code.:

Synonyms:(4S,5R)-5-Dibenzylamino-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-methylene-pentanoic acid ethyl ester

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Chemical Property of (4S,5R)-5-Dibenzylamino-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-methylene-pentanoic acid ethyl ester

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Technology Process of (4S,5R)-5-Dibenzylamino-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-methylene-pentanoic acid ethyl ester

There total 9 articles about (4S,5R)-5-Dibenzylamino-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-methylene-pentanoic acid ethyl ester 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: 82.0%

: 205489-05-0
(S)-5-Dibenzylamino-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methylene-4-oxo-pentanoic acid ethyl ester

: 205489-06-1
(4S,5R)-5-Dibenzylamino-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-methylene-pentanoic acid ethyl ester

Guidance literature:: With sodium tetrahydroborate; In ethanol; at -10 ℃; for 1.5h;
DOI:10.1039/a708594j

Reference yield:

: 114185-07-8
ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate

: 205489-06-1
(4S,5R)-5-Dibenzylamino-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-methylene-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.75 h / -50 - -10 °C

2: 80 percent / LiN₃ / dimethylformamide / 3 h / 18 °C

3: 100 percent / LAH / tetrahydrofuran / 3 h / 18 - 65 °C

4: 90 percent / K₂CO₃ / acetonitrile / 14 h / 60 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 to 0 deg C, 1 h, 2.) CH₂Cl₂

6: 87 percent / Zn, H₂O, NH₄Cl / tetrahydrofuran / 0.75 h / 60 °C

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 to 0 deg C, 1 h, 2.) CH₂Cl₂

8: 82 percent / NaBH₄ / ethanol / 1.5 h / -10 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; lithium azide; oxalyl dichloride; water; potassium carbonate; ammonium chloride; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/a708594j

Reference yield:

: 205489-00-5
(R)-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-trifluoromethanesulfonyloxy-acetic acid ethyl ester

: 205489-06-1
(4S,5R)-5-Dibenzylamino-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-methylene-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / LiN₃ / dimethylformamide / 3 h / 18 °C

2: 100 percent / LAH / tetrahydrofuran / 3 h / 18 - 65 °C

3: 90 percent / K₂CO₃ / acetonitrile / 14 h / 60 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 to 0 deg C, 1 h, 2.) CH₂Cl₂

5: 87 percent / Zn, H₂O, NH₄Cl / tetrahydrofuran / 0.75 h / 60 °C

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 to 0 deg C, 1 h, 2.) CH₂Cl₂

7: 82 percent / NaBH₄ / ethanol / 1.5 h / -10 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; lithium azide; oxalyl dichloride; water; potassium carbonate; ammonium chloride; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/a708594j