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

Base Information

• Chemical Name: meso-(1r,2R,6S)-1-acetamido-2,6-diacetoxycyclohexane-1-acetaldehyde 1,3-propanediol acetal
• CAS No.: 244153-92-2
• Molecular Formula: C₁₇H₂₇NO₇
• Molecular Weight: 357.404
• Mol file: 244153-92-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about meso-(1r,2R,6S)-1-acetamido-2,6-diacetoxycyclohexane-1-acetaldehyde 1,3-propanediol acetal 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:

2-(2-nitroethyl)-1,3-dioxane (146073-16-7) → meso-(1r,2R,6S)-1-acetamido-2,6-diacetoxycyclohexane-1-acetaldehyde 1,3-propanediol acetal (244153-92-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / 1,1,3,3-tetramethylguanidine / tetrahydrofuran

2: 81 percent / DMAP / CH₂Cl₂ / 2 h

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

4: 3.24 g / pyridine / 1 h / Heating

With pyridine; dmap; hydrogen; N,N,N',N'-tetramethylguanidine; nickel; In tetrahydrofuran; dichloromethane; 1: tandem Henry condensation / 2: Acetylation / 3: Reduction / 4: Acetylation;

DOI:10.1021/jo990293i

Reference yield:

meso-(1r,2R,6S)-1-nitrocyclohexane-2,6-diol-1-acetaldehyde 1,3-propanediol acetal (244153-85-3) → meso-(1r,2R,6S)-1-acetamido-2,6-diacetoxycyclohexane-1-acetaldehyde 1,3-propanediol acetal (244153-92-2)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; dmap; hydrogen; nickel; In tetrahydrofuran; dichloromethane; 1: Acetylation / 2: Reduction / 3: Acetylation;

DOI:10.1021/jo990293i

Reference yield:

meso-(1r,2R,6S)-2,6-diacetoxy-1-nitrocyclohexane-1-acetaldehyde 1,3-propanediol acetal (244153-90-0) → meso-(1r,2R,6S)-1-acetamido-2,6-diacetoxycyclohexane-1-acetaldehyde 1,3-propanediol acetal (244153-92-2)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 3.24 g / pyridine / 1 h / Heating

With pyridine; hydrogen; nickel; In tetrahydrofuran; 1: Reduction / 2: Acetylation;

DOI:10.1021/jo990293i

upstream raw materials:

acetic anhydride

2-(2-nitroethyl)-1,3-dioxane

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

Downstream raw materials:

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

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

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

4-((1R,2R,6S)-1-Amino-2,6-dihydroxy-cyclohexyl)-butyric acid