Butanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(4-methoxyphenoxy)-2-(phen ylmethoxy)-, ethyl ester, (2S,3R)-

Base Information

• Chemical Name: Butanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(4-methoxyphenoxy)-2-(phen ylmethoxy)-, ethyl ester, (2S,3R)-
• CAS No.: 825633-61-2
• Molecular Formula: C25H33NO7
• Molecular Weight: 459.54
• Mol file: 825633-61-2.mol

Synonyms:

Chemical Property of Butanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(4-methoxyphenoxy)-2-(phen ylmethoxy)-, ethyl ester, (2S,3R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Butanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(4-methoxyphenoxy)-2-(phen ylmethoxy)-, ethyl ester, (2S,3R)-

There total 4 articles about Butanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(4-methoxyphenoxy)-2-(phen ylmethoxy)-, ethyl ester, (2S,3R)- 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:

di-tert-butyl dicarbonate (24424-99-5) + benzyl chloride (100-44-7) + (2S,3R)-3-Acetylamino-2-hydroxy-4-(4-methoxy-phenoxy)-butyric acid ethyl ester (544455-39-2) → (2S,3R)-2-Benzyloxy-3-tert-butoxycarbonylamino-4-(4-methoxy-phenoxy)-butyric acid ethyl ester (825633-61-2)

Guidance literature:

benzyl chloride; (2S,3R)-3-Acetylamino-2-hydroxy-4-(4-methoxy-phenoxy)-butyric acid ethyl ester; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 10h;

di-tert-butyl dicarbonate; With dmap; In tetrahydrofuran; for 4h; Heating;

With hydrazine; In methanol; for 4h;

DOI:10.1016/j.tetlet.2005.10.074

Reference yield:

ethyl (2E)-4-(4-methoxyphenoxy)but-2-enoate (544455-38-1) → (2S,3R)-2-Benzyloxy-3-tert-butoxycarbonylamino-4-(4-methoxy-phenoxy)-butyric acid ethyl ester (825633-61-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

2.2: DMAP / tetrahydrofuran / 4 h / Heating

2.3: NH₂NH₂ / methanol / 4 h

With lithium hydroxide; potassium osmate(VI); sodium hydride; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/j.tetlet.2005.10.074

Reference yield:

(2S,3R)-3-Acetylamino-2-benzyloxy-4-(4-methoxy-phenoxy)-butyric acid ethyl ester (596128-74-4) → (2S,3R)-2-Benzyloxy-3-tert-butoxycarbonylamino-4-(4-methoxy-phenoxy)-butyric acid ethyl ester (825633-61-2)

Guidance literature:

Multi-step reaction with 2 steps

1: DMAP / tetrahydrofuran / 4 h / Heating

2: H₂NNH₂ / methanol / 4 h

With dmap; hydrazine; In tetrahydrofuran; methanol;

DOI:10.1055/s-2004-832804

upstream raw materials:

di-tert-butyl dicarbonate

benzyl chloride

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

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

Downstream raw materials:

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

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

Toluene-4-sulfonic acid (E)-(5S,6S,7R)-6-benzyloxy-7-tert-butoxycarbonylamino-5-hydroxy-8-(4-methoxy-phenoxy)-oct-3-enyl ester