(2R,3S,4R,5R)-3-Benzyloxy-4-hydroxy-5-hydroxymethyl-2-(4-methoxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2R,3S,4R,5R)-3-Benzyloxy-4-hydroxy-5-hydroxymethyl-2-(4-methoxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:825633-71-4
Molecular Formula:C₂₅H₃₃NO₇
Molecular Weight:459.54
Hs Code.:

Synonyms:(2R,3S,4R,5R)-3-Benzyloxy-4-hydroxy-5-hydroxymethyl-2-(4-methoxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2R,3S,4R,5R)-3-Benzyloxy-4-hydroxy-5-hydroxymethyl-2-(4-methoxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2R,3S,4R,5R)-3-Benzyloxy-4-hydroxy-5-hydroxymethyl-2-(4-methoxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 10 articles about (2R,3S,4R,5R)-3-Benzyloxy-4-hydroxy-5-hydroxymethyl-2-(4-methoxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl 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: 85.0%

: 825633-70-3
(2R,3S,4R,5R)-3-Benzyloxy-4-hydroxy-2-(4-methoxy-phenoxymethyl)-5-(2,2,6,6-tetramethyl-piperidin-1-yloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 825633-71-4
(2R,3S,4R,5R)-3-Benzyloxy-4-hydroxy-5-hydroxymethyl-2-(4-methoxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With acetic acid; zinc; In tetrahydrofuran; at 80 ℃; for 1h;
DOI:10.1055/s-2004-832804

Reference yield:

: 544455-38-1
ethyl (2E)-4-(4-methoxyphenoxy)but-2-enoate

: 825633-71-4
(2R,3S,4R,5R)-3-Benzyloxy-4-hydroxy-5-hydroxymethyl-2-(4-methoxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 70 percent / K₂OsO₄*2H₂O; (DHQD)2PHAL; aq. LiOH / 2-methyl-propan-2-ol / 8 h / 4 °C

2.1: 78 percent / NaH / dimethylformamide / 10 h / 0 °C

3.1: DMAP / tetrahydrofuran / 4 h / Heating

4.1: H₂NNH₂ / methanol / 4 h

5.1: 90 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

6.1: 60 percent / tetrahydrofuran / 2 h / -50 - 20 °C

7.1: PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran

8.1: K₂CO₃ / methanol

9.1: Hg(CF₃SO₃)2 / tetrahydrofuran / -78 °C

9.2: O₂; NaBH₄ / methanol / 0.25 h

10.1: 85 percent / Zn; aq. AcOH / tetrahydrofuran / 1 h / 80 °C

With dmap; lithium hydroxide; potassium osmate(VI); di-isopropyl azodicarboxylate; Hg(CF₃SO₃)2; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; hydrazine; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 7.1: Mitsunobu reaction;
DOI:10.1055/s-2004-832804

Reference yield:

: 596128-74-4
(2S,3R)-3-Acetylamino-2-benzyloxy-4-(4-methoxy-phenoxy)-butyric acid ethyl ester

: 825633-71-4
(2R,3S,4R,5R)-3-Benzyloxy-4-hydroxy-5-hydroxymethyl-2-(4-methoxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: DMAP / tetrahydrofuran / 4 h / Heating

2.1: H₂NNH₂ / methanol / 4 h

3.1: 90 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

4.1: 60 percent / tetrahydrofuran / 2 h / -50 - 20 °C

5.1: PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran

6.1: K₂CO₃ / methanol

7.1: Hg(CF₃SO₃)2 / tetrahydrofuran / -78 °C

7.2: O₂; NaBH₄ / methanol / 0.25 h

8.1: 85 percent / Zn; aq. AcOH / tetrahydrofuran / 1 h / 80 °C

With dmap; di-isopropyl azodicarboxylate; Hg(CF₃SO₃)2; diisobutylaluminium hydride; potassium carbonate; acetic acid; triphenylphosphine; hydrazine; zinc; In tetrahydrofuran; methanol; dichloromethane; 5.1: Mitsunobu reaction;
DOI:10.1055/s-2004-832804