(2S,3S,4S)-methyl 2,3-bis(benzyloxy)-4-dimethylamino-5-methoxypentanoate

Base Information

• Chemical Name: (2S,3S,4S)-methyl 2,3-bis(benzyloxy)-4-dimethylamino-5-methoxypentanoate
• CAS No.: 180780-60-3
• Molecular Formula: C₂₃H₃₁NO₅
• Molecular Weight: 401.503
• Mol file: 180780-60-3.mol

Synonyms:(2S,3S,4S)-methyl 2,3-bis(benzyloxy)-4-dimethylamino-5-methoxypentanoate

Chemical Property of (2S,3S,4S)-methyl 2,3-bis(benzyloxy)-4-dimethylamino-5-methoxypentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-methyl 2,3-bis(benzyloxy)-4-dimethylamino-5-methoxypentanoate

There total 4 articles about (2S,3S,4S)-methyl 2,3-bis(benzyloxy)-4-dimethylamino-5-methoxypentanoate 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: 97.0%

(2S,3S,4S)-2,3-Bis-benzyloxy-4-dimethylamino-5-methoxy-pentanoic acid (180780-69-2) + diazomethyl-trimethyl-silane (18107-18-1) → (2S,3S,4S)-methyl 2,3-bis(benzyloxy)-4-dimethylamino-5-methoxypentanoate (180780-60-3)

Guidance literature:

With hydrogenchloride; In hexane; dichloromethane;

DOI:10.1021/jo960315q

Reference yield:

(2R,3S,4S)-2,3-Bis-benzyloxy-4-dimethylamino-5-methoxy-pentan-1-ol (180780-68-1) → (2S,3S,4S)-methyl 2,3-bis(benzyloxy)-4-dimethylamino-5-methoxypentanoate (180780-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 38 percent / CrO₃, H₂SO₄ / acetone / 5 h

2: 97 percent / aq. HCl / CH₂Cl₂; hexane

With chromium(VI) oxide; hydrogenchloride; sulfuric acid; In hexane; dichloromethane; acetone;

DOI:10.1021/jo960315q

Reference yield:

[(1S,2S,3R)-2,3-Bis-benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethyl-butyl]-dimethyl-amine (180780-67-0) → (2S,3S,4S)-methyl 2,3-bis(benzyloxy)-4-dimethylamino-5-methoxypentanoate (180780-60-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / TBAF / tetrahydrofuran / 8 h / Ambient temperature

2: 38 percent / CrO₃, H₂SO₄ / acetone / 5 h

3: 97 percent / aq. HCl / CH₂Cl₂; hexane

With chromium(VI) oxide; hydrogenchloride; sulfuric acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; dichloromethane; acetone;

DOI:10.1021/jo960315q

upstream raw materials:

(2S,3S,4S)-2,3-Bis-benzyloxy-4-dimethylamino-5-methoxy-pentanoic acid

diazomethyl-trimethyl-silane

(2R,3S,4S)-2,3-Bis-benzyloxy-4-dimethylamino-5-methoxy-pentan-1-ol

[(1S,2S,3R)-2,3-Bis-benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethyl-butyl]-dimethyl-amine

Downstream raw materials:

(2S,3S,4S)-2,3-Bis-benzyloxy-4-dimethylamino-5-methoxy-pentanoic acid [(1R,3S)-3-(4-chloromethyl-oxazol-2-yl)-1-methyl-butyl]-amide