Cyclohexanebutanoic acid, 1-amino-2,6-dihydroxy-, (2R,6S)-rel- (9CI)

Base Information

• Chemical Name: Cyclohexanebutanoic acid, 1-amino-2,6-dihydroxy-, (2R,6S)-rel- (9CI)
• CAS No.: 244154-24-3
• Molecular Formula: C10H19 N O4
• Molecular Weight: 217.26
• Mol file: 244154-24-3.mol

Synonyms:Cyclohexanebutanoicacid, 1-amino-2,6-dihydroxy-, (2R,6S)-rel- (9CI)

Chemical Property of Cyclohexanebutanoic acid, 1-amino-2,6-dihydroxy-, (2R,6S)-rel- (9CI)

Chemical Property:

• PSA: 103.78000
• LogP: 0.54480

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclohexanebutanoic acid, 1-amino-2,6-dihydroxy-, (2R,6S)-rel- (9CI)

There total 8 articles about Cyclohexanebutanoic acid, 1-amino-2,6-dihydroxy-, (2R,6S)-rel- (9CI) 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:

meso-(1r,2R,6S)-1-nitrocyclohexane-2,6-diol-1-acetaldehyde 1,3-propanediol acetal (244153-85-3) → 4-((1R,2R,6S)-1-Amino-2,6-dihydroxy-cyclohexyl)-butyric acid (244154-24-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 81 percent / DMAP / CH₂Cl₂ / 2 h

2: hydrogen / Raney nickel / tetrahydrofuran / 14 h / 60 °C / 760 Torr

3: 3.24 g / pyridine / 1 h / Heating

4: aqueous acetic acid / 1 h / 20 °C / ultrasound

5: 144 mg / triethylamine / CH₂Cl₂ / 14 h / 20 °C

6: 96 percent / hydrogen / palladium on activated charcoal / methanol / 18 h / 20 °C / 760 Torr

7: aq. HCl / 48 h / Heating

With pyridine; hydrogenchloride; dmap; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; nickel; In tetrahydrofuran; methanol; dichloromethane; 1: Acetylation / 2: Reduction / 3: Acetylation / 4: deacetalization / 5: Wittig olefination / 6: Catalytic hydrogenation / 7: Hydrolysis;

DOI:10.1021/jo990293i

Reference yield:

(1S,2R,3R)-2-Amino-2-[1,3]dioxan-2-ylmethyl-cyclohexane-1,3-diol → 4-((1R,2R,6S)-1-Amino-2,6-dihydroxy-cyclohexyl)-butyric acid (244154-24-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 47.0 mg / pyridine / 1 h / Heating

2: aqueous acetic acid / 1 h / 20 °C / ultrasound

3: 144 mg / triethylamine / CH₂Cl₂ / 14 h / 20 °C

4: 96 percent / hydrogen / palladium on activated charcoal / methanol / 18 h / 20 °C / 760 Torr

5: aq. HCl / 48 h / Heating

With pyridine; hydrogenchloride; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; 1: Acetylation / 2: deacetalization / 3: Wittig olefination / 4: Catalytic hydrogenation / 5: Hydrolysis;

DOI:10.1021/jo990293i

Reference yield:

Acetic acid (1R,2R,3S)-3-acetoxy-2-acetylamino-2-(2-oxo-ethyl)-cyclohexyl ester → 4-((1R,2R,6S)-1-Amino-2,6-dihydroxy-cyclohexyl)-butyric acid (244154-24-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 144 mg / triethylamine / CH₂Cl₂ / 14 h / 20 °C

2: 96 percent / hydrogen / palladium on activated charcoal / methanol / 18 h / 20 °C / 760 Torr

3: aq. HCl / 48 h / Heating

With hydrogenchloride; hydrogen; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; 1: Wittig olefination / 2: Catalytic hydrogenation / 3: Hydrolysis;

DOI:10.1021/jo990293i

upstream raw materials:

meso-(E)-(1r,2R,6S)-1-acetamido-2,6-diacetoxycyclohexanebutanoic acid ethyl ester

meso-(1r,2R,6S)-1-nitrocyclohexane-2,6-diol-1-acetaldehyde 1,3-propanediol acetal

meso-(1r,2R,6S)-2,6-diacetoxy-1-nitrocyclohexane-1-acetaldehyde 1,3-propanediol acetal

meso-(1r,2R,6S)-1-acetamido-2,6-diacetoxycyclohexane-1-acetaldehyde 1,3-propanediol acetal

Downstream raw materials:

(-)-(6S,12S)-12-phenoxythionocarbonyloxy-7-aza-1,4-dioxadispiro[4,0,5,4]pentadecan-8-one