(1R,2R,6S,7R,7aR)-2-benzyloxy-6,7-isopropylidenedioxy-1-methoxypyrrolizidine

Base Information

• Chemical Name: (1R,2R,6S,7R,7aR)-2-benzyloxy-6,7-isopropylidenedioxy-1-methoxypyrrolizidine
• CAS No.: 1608130-52-4
• Molecular Formula: C₁₈H₂₅NO₄
• Molecular Weight: 319.401

Synonyms:(1R,2R,6S,7R,7aR)-2-benzyloxy-6,7-isopropylidenedioxy-1-methoxypyrrolizidine

Chemical Property of (1R,2R,6S,7R,7aR)-2-benzyloxy-6,7-isopropylidenedioxy-1-methoxypyrrolizidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (1R,2R,6S,7R,7aR)-2-benzyloxy-6,7-isopropylidenedioxy-1-methoxypyrrolizidine

There total 11 articles about (1R,2R,6S,7R,7aR)-2-benzyloxy-6,7-isopropylidenedioxy-1-methoxypyrrolizidine 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: 60.0%

(1'R,2'R,3aR,4R,6aS)-4-(2'-benzyloxy-3'-hydroxy-1'-methoxypropyl)-2,2-dimethyltetrahydro[1,3]dioxolo[4,5-c]pyrrole (1608130-50-2) + methanesulfonyl chloride (124-63-0) → (1R,2R,6S,7R,7aR)-2-benzyloxy-6,7-isopropylidenedioxy-1-methoxypyrrolizidine (1608130-52-4) + (1'R,2'R,3aR,4R,6aS)-4-(2'-benzyloxy-3'-methylsulfonyloxy-1'-methoxypropyl)-2,2-dimethyl-5-methylsulfonyl-tetrahydro[1,3]dioxolo[4,5-c]pyrrole

Guidance literature:

With pyridine; In tetrahydrofuran; at 0 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/ejoc.201301406

Reference yield:

(3R,4R,4aR,5R,6S)-5,6-isopropylidenedioxy-4-methoxyhexahydropyrrolo[1,2-b][1,2]oxazin-3-ol (1608130-36-4) → (1R,2R,6S,7R,7aR)-2-benzyloxy-6,7-isopropylidenedioxy-1-methoxypyrrolizidine (1608130-52-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere

2: samarium diiodide / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

3: pyridine / 24 h / 0 - 20 °C / Inert atmosphere

With pyridine; samarium diiodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/ejoc.201301406

Reference yield:

benzyl bromide (100-39-0) → (1R,2R,6S,7R,7aR)-2-benzyloxy-6,7-isopropylidenedioxy-1-methoxypyrrolizidine (1608130-52-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere

2: samarium diiodide / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

3: pyridine / 24 h / 0 - 20 °C / Inert atmosphere

With pyridine; samarium diiodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/ejoc.201301406

upstream raw materials:

(4aS,5R,6S)-5,6-isopropylidenedioxy-4-methoxy-4a,5,6,7-tetrahydro-2H-pyrrolo[1,2-b][1,2]oxazine

benzyl bromide

(3R,4R,4aR,5R,6S)-3-benzyloxy-5,6-isopropylidenedioxy-4-methoxyhexahydropyrrolo[1,2-b][1,2]oxazine

(3S,4R)-3,4-O-isopropylidenedioxy-1-pyrroline-N-oxide

Downstream raw materials:

(1R,2S,6R,7R,7aS)-6-(benzyloxy)-7-methoxyhexahydro-1H-pyrrolizine-1,2-diol

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