(2S,3S_.6R)-2-allyl-2-((S)-1-(but-3-enyloxy)propan-2-yl)-4,5-dimethyl-6-phenylnorpholin-3-one

Base Information

• Chemical Name: (2S,3S_.6R)-2-allyl-2-((S)-1-(but-3-enyloxy)propan-2-yl)-4,5-dimethyl-6-phenylnorpholin-3-one
• CAS No.: 916607-06-2
• Molecular Formula: C₂₂H₃₁NO₃
• Molecular Weight: 357.493

Synonyms:(2S,3S_.6R)-2-allyl-2-((S)-1-(but-3-enyloxy)propan-2-yl)-4,5-dimethyl-6-phenylnorpholin-3-one

Chemical Property of (2S,3S_.6R)-2-allyl-2-((S)-1-(but-3-enyloxy)propan-2-yl)-4,5-dimethyl-6-phenylnorpholin-3-one

Chemical Property:

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Technology Process of (2S,3S_.6R)-2-allyl-2-((S)-1-(but-3-enyloxy)propan-2-yl)-4,5-dimethyl-6-phenylnorpholin-3-one

There total 4 articles about (2S,3S_.6R)-2-allyl-2-((S)-1-(but-3-enyloxy)propan-2-yl)-4,5-dimethyl-6-phenylnorpholin-3-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: 76.0%

(5R,6R,8R,9S)-8-phenyl-5,9,10-trimethyl-1,3,7-trioxa-10-azaspiro[5.5]undecan-11-one (916607-05-1) + allyl-trimethyl-silane (762-72-1) → (2S,3S.6R)-2-allyl-2-((S)-1-(but-3-enyloxy)propan-2-yl)-4,5-dimethyl-6-phenylnorpholin-3-one (916607-06-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ol062484v

Reference yield:

(5S,6R)-2-Ethyl-2-hydroxy-4,5-dimethyl-6-phenyl-morpholin-3-one → (2S,3S.6R)-2-allyl-2-((S)-1-(but-3-enyloxy)propan-2-yl)-4,5-dimethyl-6-phenylnorpholin-3-one (916607-06-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.9 g / BF₃*OEt₂ / CH₂Cl₂ / 18 h / 20 °C

2: 45 percent / H₂SO₄; glacial AcOH / 8 h / 85 °C

3: 76 percent / BF₃*Et₂O / CH₂Cl₂ / -78 - 20 °C

With sulfuric acid; boron trifluoride diethyl etherate; acetic acid; In dichloromethane; 2: Prins reaction;

DOI:10.1021/ol062484v

Reference yield:

(Z,5S,6R)-2-ethylidene-4,5-dimethyl-6-phenylmorpholin-3-one (207223-30-1) → (2S,3S.6R)-2-allyl-2-((S)-1-(but-3-enyloxy)propan-2-yl)-4,5-dimethyl-6-phenylnorpholin-3-one (916607-06-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / H₂SO₄; glacial AcOH / 8 h / 85 °C

2: 76 percent / BF₃*Et₂O / CH₂Cl₂ / -78 - 20 °C

With sulfuric acid; boron trifluoride diethyl etherate; acetic acid; In dichloromethane; 1: Prins reaction;

DOI:10.1021/ol062484v

upstream raw materials:

(5R,6R,8R,9S)-8-phenyl-5,9,10-trimethyl-1,3,7-trioxa-10-azaspiro[5.5]undecan-11-one

allyl-trimethyl-silane

(Z,5S,6R)-2-ethylidene-4,5-dimethyl-6-phenylmorpholin-3-one

(5S,6R)-4,5-dimethyl-6-phenyl-morpholin-2,3-dione

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