[(1R,2S,3R)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(1R,2S,3R)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester
• CAS No.: 825633-63-4
• Molecular Formula: C₂₅H₃₃NO₆
• Molecular Weight: 443.54
• Mol file: 825633-63-4.mol

Synonyms:[(1R,2S,3R)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester

Chemical Property of [(1R,2S,3R)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2S,3R)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester

There total 8 articles about [(1R,2S,3R)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic 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:

4-Nitro-benzoic acid (1R,2S,3R)-2-benzyloxy-3-tert-butoxycarbonylamino-4-(4-methoxy-phenoxy)-1-vinyl-butyl ester → [(1R,2S,3R)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester (825633-63-4)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1055/s-2004-832804

Reference yield:

ethyl (2E)-4-(4-methoxyphenoxy)but-2-enoate (544455-38-1) → [(1R,2S,3R)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester (825633-63-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 70 percent / K₂OsO₄*2H₂O; (DHQD)2PHAL; aq. LiOH / 2-methyl-propan-2-ol / 8 h / 4 °C

2: 78 percent / NaH / dimethylformamide / 10 h / 0 °C

3: DMAP / tetrahydrofuran / 4 h / Heating

4: H₂NNH₂ / methanol / 4 h

5: 90 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

6: 60 percent / tetrahydrofuran / 2 h / -50 - 20 °C

7: PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran

8: K₂CO₃ / methanol

With dmap; lithium hydroxide; potassium osmate(VI); di-isopropyl azodicarboxylate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; hydrazine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 7: Mitsunobu reaction;

DOI:10.1055/s-2004-832804

Reference yield:

(2S,3R)-3-Acetylamino-2-benzyloxy-4-(4-methoxy-phenoxy)-butyric acid ethyl ester (596128-74-4) → [(1R,2S,3R)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester (825633-63-4)

Guidance literature:

Multi-step reaction with 6 steps

1: DMAP / tetrahydrofuran / 4 h / Heating

2: H₂NNH₂ / methanol / 4 h

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

4: 60 percent / tetrahydrofuran / 2 h / -50 - 20 °C

5: PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran

6: K₂CO₃ / methanol

With dmap; di-isopropyl azodicarboxylate; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; hydrazine; In tetrahydrofuran; methanol; dichloromethane; 5: Mitsunobu reaction;

DOI:10.1055/s-2004-832804

upstream raw materials:

ethyl (2E)-4-(4-methoxyphenoxy)but-2-enoate

(2S,3R)-3-Acetylamino-2-hydroxy-4-(4-methoxy-phenoxy)-butyric acid ethyl ester

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

[(1R,2S)-2-Benzyloxy-1-(4-methoxy-phenoxymethyl)-3-oxo-propyl]-carbamic acid tert-butyl ester

Downstream raw materials:

(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

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