(2S,3S)-N,2-O-Dibenzyl-3,4-O-isopropylidene-L-threose imine

Base Information

• Chemical Name: (2S,3S)-N,2-O-Dibenzyl-3,4-O-isopropylidene-L-threose imine
• CAS No.: 186465-19-0
• Molecular Formula: C₂₁H₂₅NO₃
• Molecular Weight: 339.434
• Mol file: 186465-19-0.mol

Synonyms:(2S,3S)-N,2-O-Dibenzyl-3,4-O-isopropylidene-L-threose imine

Chemical Property of (2S,3S)-N,2-O-Dibenzyl-3,4-O-isopropylidene-L-threose imine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-N,2-O-Dibenzyl-3,4-O-isopropylidene-L-threose imine

There total 1 articles about (2S,3S)-N,2-O-Dibenzyl-3,4-O-isopropylidene-L-threose imine 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: 100.0%

2-O-benzyl-3,4-O-isopropylidene-L-threose (100906-42-1) + benzylamine (100-46-9) → (2S,3S)-N,2-O-Dibenzyl-3,4-O-isopropylidene-L-threose imine (186465-19-0)

Guidance literature:

With aluminum oxide; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1055/s-1999-3661

Reference yield:

(2S,3S)-N,2-O-Dibenzyl-3,4-O-isopropylidene-L-threose imine (186465-19-0) → (2R,3S,4S)-3-Acetoxy-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)pyrrolidine (180081-83-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Mg; I₂ / diethyl ether / 0.25 h / Heating

1.2: diethyl ether / 3 h / 20 °C

2.1: H₂O; HCl / dioxane / 20 °C

3.1: 77 percent / DEAD; PPh₃; pyridine / 1.5 h / 0 °C

4.1: 98 percent / imidazole / dimethylformamide / 17 h / 50 °C

5.1: H₂ / 10 percent Pd(OH)2/C / dioxane / 72 h / 20 °C / 3000.24 Torr

6.1: H₂ / 10 percent Pd(OH)2/C / dioxane; acetic acid / 24 h / 20 °C

7.1: 94 percent / pyridine; DMAP / 3 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; water; hydrogen; iodine; magnesium; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In 1,4-dioxane; diethyl ether; acetic acid; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Grignard reaction / 2.1: Hydrolysis / 3.1: Cyclization / 4.1: Etherification / 5.1: Catalytic hydrogenation / 6.1: Hydrogenolysis / 7.1: Acetylation;

DOI:10.1055/s-1999-3661

Reference yield:

(2S,3S)-N,2-O-Dibenzyl-3,4-O-isopropylidene-L-threose imine (186465-19-0) → 2-benzyl-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (249617-10-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Mg / diethyl ether / 0.25 h / Heating

1.2: diethyl ether / 3 h / 20 °C

2.1: H₂O; HCl / dioxane / 20 °C

3.1: 79 percent / DEAD; PPh₃; pyridine / 1.5 h / 0 °C

4.1: 94 percent / imidazole / dimethylformamide / 20 h / 50 °C

5.1: H₂ / 10 percent Pd(OH)2/C / dioxane / 144 h / 20 °C / 3000.24 Torr

With pyridine; 1H-imidazole; hydrogenchloride; water; hydrogen; magnesium; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In 1,4-dioxane; diethyl ether; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Grignard reaction / 2.1: Hydrolysis / 3.1: Cyclization / 4.1: Etherification / 5.1: Catalytic hydrogenation;

DOI:10.1055/s-1999-3661

upstream raw materials:

2-O-benzyl-3,4-O-isopropylidene-L-threose

benzylamine

Downstream raw materials:

Benzyl-{(R)-1-[(S)-benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-pentyl}-amine

Benzyl-{(R)-1-[(S)-benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-allyl}-amine

Benzyl-{(R)-1-[(S)-benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-propyl}-amine

Benzyl-[(1S,2S)-2-benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-trimethylsilanylmethyl-ethyl]-amine