(8S,6R,7R,5S)-(8-benzyloxymethyl)-6,7-bis(benzyloxy)-3-oxa-1-azabicyclo[3.3.0]octane

Base Information

• Chemical Name: (8S,6R,7R,5S)-(8-benzyloxymethyl)-6,7-bis(benzyloxy)-3-oxa-1-azabicyclo[3.3.0]octane
• CAS No.: 1373335-71-7
• Molecular Formula: C₂₈H₃₁NO₄
• Molecular Weight: 445.558
• Mol file: 1373335-71-7.mol

Synonyms:(8S,6R,7R,5S)-(8-benzyloxymethyl)-6,7-bis(benzyloxy)-3-oxa-1-azabicyclo[3.3.0]octane

Chemical Property of (8S,6R,7R,5S)-(8-benzyloxymethyl)-6,7-bis(benzyloxy)-3-oxa-1-azabicyclo[3.3.0]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8S,6R,7R,5S)-(8-benzyloxymethyl)-6,7-bis(benzyloxy)-3-oxa-1-azabicyclo[3.3.0]octane

There total 2 articles about (8S,6R,7R,5S)-(8-benzyloxymethyl)-6,7-bis(benzyloxy)-3-oxa-1-azabicyclo[3.3.0]octane 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: 94.0%

(2S,3R,4R,5S)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-2-(hydroxymethyl)pyrrolidine (881185-77-9) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → (8S,6R,7R,5S)-(8-benzyloxymethyl)-6,7-bis(benzyloxy)-3-oxa-1-azabicyclo[3.3.0]octane (1373335-71-7)

Guidance literature:

With acetic acid; In 1,4-dioxane; at 60 ℃; for 0.5h;

DOI:10.1021/jo3004452

Reference yield:

(2S,3R,4R,5S)-2-acetoxymethyl-3,4-di-O-benzyl-5-benzyloxymethyl-N-(p-toluenesulfonamido)pyrrolidine (881185-59-7) → (8S,6R,7R,5S)-(8-benzyloxymethyl)-6,7-bis(benzyloxy)-3-oxa-1-azabicyclo[3.3.0]octane (1373335-71-7)

Guidance literature:

Multi-step reaction with 2 steps

1: magnesium / methanol / 2 h / Reflux

2: acetic acid / 1,4-dioxane / 0.5 h / 60 °C

With magnesium; acetic acid; In 1,4-dioxane; methanol;

DOI:10.1021/jo3004452

Reference yield: 68.0%

(8S,6R,7R,5S)-(8-benzyloxymethyl)-6,7-bis(benzyloxy)-3-oxa-1-azabicyclo[3.3.0]octane (1373335-71-7) → (2S,3R,4R,5S)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-2-(hydroxymethyl)-N-methylpyrrolidine (1373335-72-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃;

DOI:10.1021/jo3004452

upstream raw materials:

(2S,3R,4R,5S)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-2-(hydroxymethyl)pyrrolidine

formaldehyd

(2S,3R,4R,5S)-2-acetoxymethyl-3,4-di-O-benzyl-5-benzyloxymethyl-N-(p-toluenesulfonamido)pyrrolidine

Downstream raw materials:

(2S,3R,4R,5S)-2-(9-adeninylmethyl)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-N-methylpyrrolidine

(2S,3R,4R,5S)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-2-(hydroxymethyl)-N-methylpyrrolidine