(5R,8S,9S)-2-benzyl-8,9-dihydroxy-8-isobutyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Base Information

• Chemical Name: (5R,8S,9S)-2-benzyl-8,9-dihydroxy-8-isobutyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
• CAS No.: 1571909-22-2
• Molecular Formula: C₁₈H₂₁NO₅
• Molecular Weight: 331.368

Synonyms:(5R,8S,9S)-2-benzyl-8,9-dihydroxy-8-isobutyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Chemical Property of (5R,8S,9S)-2-benzyl-8,9-dihydroxy-8-isobutyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Chemical Property:

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Technology Process of (5R,8S,9S)-2-benzyl-8,9-dihydroxy-8-isobutyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

There total 8 articles about (5R,8S,9S)-2-benzyl-8,9-dihydroxy-8-isobutyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione 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: 65.0%

(5R,8R,9S)-2-benzyl-9-hydroxy-8-isobutyl-8-isopropoxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione → (5R,8S,9S)-2-benzyl-8,9-dihydroxy-8-isobutyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione (1571909-22-2)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water; at 20 ℃; for 16h;

DOI:10.1021/acs.orglett.9b01589

Reference yield:

(1S,4S,5S)-1-acetyl-4-hydroxy-4-isobutyl-6-oxa-3-azabicyclo[3.1.0]hexan-2-one → (5R,8S,9S)-2-benzyl-8,9-dihydroxy-8-isobutyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione (1571909-22-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: camphor-10-sulfonic acid / isopropyl alcohol / 4.5 h / 20 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -78 °C

2.2: 0.67 h / -78 °C

3.1: toluene-4-sulfonic acid / tetrahydrofuran; water / 16 h / 20 °C

With camphor-10-sulfonic acid; toluene-4-sulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran; water; isopropyl alcohol;

DOI:10.1021/acs.orglett.9b01589

Reference yield:

isobutyl glyoxal (16979-05-8) → (5R,8S,9S)-2-benzyl-8,9-dihydroxy-8-isobutyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione (1571909-22-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ytterbium(III) triflate; sodium carbonate; C₄₅H₆₈N₄O₄ / tetrahydrofuran / 48 h / 20 °C / Molecular sieve; Inert atmosphere

2.1: camphor-10-sulfonic acid / isopropyl alcohol / 4.5 h / 20 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -78 °C

3.2: 0.67 h / -78 °C

4.1: toluene-4-sulfonic acid / tetrahydrofuran; water / 16 h / 20 °C

With camphor-10-sulfonic acid; C₄₅H₆₈N₄O₄; sodium carbonate; toluene-4-sulfonic acid; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; water; isopropyl alcohol;

DOI:10.1021/acs.orglett.9b01589

upstream raw materials:

isobutyl glyoxal

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