methyl (1R,6S)-1-(3-azidopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate

Base Information

• Chemical Name: methyl (1R,6S)-1-(3-azidopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate
• CAS No.: 1416815-29-6
• Molecular Formula: C₁₉H₂₅N₃O₃
• Molecular Weight: 343.426
• Mol file: 1416815-29-6.mol

Synonyms:methyl (1R,6S)-1-(3-azidopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate

Chemical Property of methyl (1R,6S)-1-(3-azidopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1R,6S)-1-(3-azidopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate

There total 1 articles about methyl (1R,6S)-1-(3-azidopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate 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:

methyl (1R,6S)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate (954148-38-0) + 1-azido-3-iodopropane (58503-62-1) → methyl (1R,6S)-1-(3-azidopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate (1416815-29-6)

Guidance literature:

methyl (1R,6S)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 2h; Inert atmosphere;

1-azido-3-iodopropane; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ol3030764

Reference yield:

methyl (1R,6S)-1-(3-azidopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate (1416815-29-6) → (6R,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-en-1-one (1416815-14-9)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; water / tetrahydrofuran / 2 h / Reflux; Inert atmosphere

2: potassium carbonate / methanol; water / 18 h / 20 °C / Inert atmosphere

With water; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; water; 1: |Staudinger Azide Reduction;

DOI:10.1021/ol3030764

Reference yield:

methyl (1R,6S)-1-(3-azidopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate (1416815-29-6) → (6S,7S,11S)-11-(benzyloxymethyl)-7-hydroxy-2-azaspiro[5.5]undec-8-en-1-one (1416815-15-0)

Guidance literature:

Multi-step reaction with 3 steps

1: triphenylphosphine; water / tetrahydrofuran / 2 h / Reflux; Inert atmosphere

2: potassium carbonate / methanol; water / 18 h / 20 °C / Inert atmosphere

3: selenium(IV) oxide; water / ethanol / 72 h / 90 °C / Inert atmosphere

With selenium(IV) oxide; water; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; water; 1: |Staudinger Azide Reduction;

DOI:10.1021/ol3030764

upstream raw materials:

methyl (1R,6S)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate

1-azido-3-iodopropane

Downstream raw materials:

(6R,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-en-1-one

(6S,7S,11S)-11-(benzyloxymethyl)-7-hydroxy-2-azaspiro[5.5]undec-8-en-1-one

methyl (1R,6S)-1-(3-aminopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate

(6S,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-ene-1,7-dione