(1R,5S,6S,7S,7aS)-6,7-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydro-1(hydroxymethyl)pyrrolo[1,2-c]-oxazol-3(1H)-one

Base Information

• Chemical Name: (1R,5S,6S,7S,7aS)-6,7-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydro-1(hydroxymethyl)pyrrolo[1,2-c]-oxazol-3(1H)-one
• CAS No.: 1450914-22-3
• Molecular Formula: C₂₉H₃₁NO₆
• Molecular Weight: 489.568

Synonyms:(1R,5S,6S,7S,7aS)-6,7-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydro-1(hydroxymethyl)pyrrolo[1,2-c]-oxazol-3(1H)-one

Chemical Property of (1R,5S,6S,7S,7aS)-6,7-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydro-1(hydroxymethyl)pyrrolo[1,2-c]-oxazol-3(1H)-one

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Technology Process of (1R,5S,6S,7S,7aS)-6,7-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydro-1(hydroxymethyl)pyrrolo[1,2-c]-oxazol-3(1H)-one

There total 3 articles about (1R,5S,6S,7S,7aS)-6,7-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydro-1(hydroxymethyl)pyrrolo[1,2-c]-oxazol-3(1H)-one 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: 85.0%

(1S,5S,6S,7S,7aS)-6,7-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydro-1-(hydroxymethyl)pyrrolo[1,2-c]oxazol-3(1H)-one → (1R,5S,6S,7S,7aS)-6,7-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydro-1(hydroxymethyl)pyrrolo[1,2-c]-oxazol-3(1H)-one (1450914-22-3)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 0.166667h;

DOI:10.3390/molecules18066723

Reference yield: 24.0%

C36H39NO7 (1309468-93-6) → C29H31NO6 (1309469-06-4) + (1R,5S,6S,7S,7aS)-6,7-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydro-1(hydroxymethyl)pyrrolo[1,2-c]-oxazol-3(1H)-one (1450914-22-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; at 20 ℃;

DOI:10.1021/acs.joc.5b00571

Reference yield:

C36H39NO7 (1309468-93-6) → (1R,5S,6S,7S,7aS)-6,7-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydro-1(hydroxymethyl)pyrrolo[1,2-c]-oxazol-3(1H)-one (1450914-22-3)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / dichloromethane / 14 h / 20 °C

2: potassium hydroxide / methanol / 0.17 h / 20 °C

3: hydrogenchloride / methanol / 0.17 h / 20 °C

With pyridine; hydrogenchloride; potassium hydroxide; In methanol; dichloromethane;

DOI:10.3390/molecules18066723

upstream raw materials:

C₃₆H₃₉NO₇

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