(1R,3R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl 4-nitrobenzoate

Base Information

• Chemical Name: (1R,3R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl 4-nitrobenzoate
• CAS No.: 1609017-81-3
• Molecular Formula: C₃₇H₃₈N₂O₇
• Molecular Weight: 622.718

Synonyms:(1R,3R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl 4-nitrobenzoate

Chemical Property of (1R,3R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl 4-nitrobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl 4-nitrobenzoate

There total 10 articles about (1R,3R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl 4-nitrobenzoate 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: 70.0%

(1R,3R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol (1214271-07-4) + 4-nitro-benzoic acid (62-23-7) → (1R,3R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl 4-nitrobenzoate (1609017-81-3)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 80 ℃; for 48h;

DOI:10.1021/jo5005923

Reference yield:

(1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1-((S)-2-(4-methoxybenzyloxy)propyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one (1214271-04-1) → (1R,3R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl 4-nitrobenzoate (1609017-81-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 4 h / 26 °C

2: sodium hydroxide; water / ethanol / 1 h / 110 °C / Microwave irradiation

3: triethylamine; methanesulfonyl chloride / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

4: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 48 h / 80 °C

With di-isopropyl azodicarboxylate; water; methanesulfonyl chloride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In ethanol; dichloromethane; water; toluene; 4: |Mitsunobu Displacement;

DOI:10.1021/jo5005923

Reference yield:

(1R,5R,6R,7S,7aS)-5-(benzyloxymethyl)-6,7-dihydroxy-1-((S)-2-(4-methoxybenzyloxy)propyl)-tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one (1214271-02-9) → (1R,3R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl 4-nitrobenzoate (1609017-81-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 0.25 h / 18 °C / Inert atmosphere

1.2: 18 h / 0 - 18 °C / Inert atmosphere

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 4 h / 26 °C

3.1: sodium hydroxide; water / ethanol / 1 h / 110 °C / Microwave irradiation

4.1: triethylamine; methanesulfonyl chloride / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

5.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 48 h / 80 °C

With di-isopropyl azodicarboxylate; water; tetra-(n-butyl)ammonium iodide; methanesulfonyl chloride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; 5.1: |Mitsunobu Displacement;

DOI:10.1021/jo5005923

upstream raw materials:

(1R,5R,6R,7S,7aS)-5-(benzyloxymethyl)-6,7-dihydroxy-1-((S)-2-(4-methoxybenzyloxy)propyl)-tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

(1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1-((S)-2-(4-methoxybenzyloxy)propyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

(1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1-((S)-2-hydroxypropyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

(1R,3S)-1-((2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-yl)butane-1,3-diol

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