(R)-3-((S)-1-Hydroxymethyl-2-methyl-propyl)-5,5-dimethyl-6-((Z)-1-methyl-4-phenyl-but-1-en-3-ynyl)-[1,3]oxazinane-2,4-dione

Base Information

• Chemical Name: (R)-3-((S)-1-Hydroxymethyl-2-methyl-propyl)-5,5-dimethyl-6-((Z)-1-methyl-4-phenyl-but-1-en-3-ynyl)-[1,3]oxazinane-2,4-dione
• CAS No.: 127743-22-0
• Molecular Formula: C₂₂H₂₇NO₄
• Molecular Weight: 369.461
• Mol file: 127743-22-0.mol

Synonyms:(R)-3-((S)-1-Hydroxymethyl-2-methyl-propyl)-5,5-dimethyl-6-((Z)-1-methyl-4-phenyl-but-1-en-3-ynyl)-[1,3]oxazinane-2,4-dione

Chemical Property of (R)-3-((S)-1-Hydroxymethyl-2-methyl-propyl)-5,5-dimethyl-6-((Z)-1-methyl-4-phenyl-but-1-en-3-ynyl)-[1,3]oxazinane-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-((S)-1-Hydroxymethyl-2-methyl-propyl)-5,5-dimethyl-6-((Z)-1-methyl-4-phenyl-but-1-en-3-ynyl)-[1,3]oxazinane-2,4-dione

There total 5 articles about (R)-3-((S)-1-Hydroxymethyl-2-methyl-propyl)-5,5-dimethyl-6-((Z)-1-methyl-4-phenyl-but-1-en-3-ynyl)-[1,3]oxazinane-2,4-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: 18.0%

(S)-3-(2-bromo-2-methylpropanoyl)-4-isopropyloxazolidin-2-one (127232-32-0) + (Z)-2-methyl-5-phenylpent-2-en-4-ynal (127743-21-9) → (S)-3-Isobutyryl-4-isopropyl-oxazolidin-2-one (127743-18-4) + (R)-3-((S)-1-Hydroxymethyl-2-methyl-propyl)-5,5-dimethyl-6-((Z)-1-methyl-4-phenyl-but-1-en-3-ynyl)-[1,3]oxazinane-2,4-dione (127743-22-0)

Guidance literature:

With lithium aluminium tetrahydride; tin(ll) chloride; In tetrahydrofuran; for 18h; Ambient temperature;

DOI:10.1016/S0040-4039(01)93480-X

Reference yield:

(4S)-4-isopropyl-1,3-oxazolidin-2-one (17016-83-0) → (R)-3-((S)-1-Hydroxymethyl-2-methyl-propyl)-5,5-dimethyl-6-((Z)-1-methyl-4-phenyl-but-1-en-3-ynyl)-[1,3]oxazinane-2,4-dione (127743-22-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / ⁿBuLi / tetrahydrofuran / -78 °C

2: 18 percent / SnCl₂, LiAlH₄ / tetrahydrofuran / 18 h / Ambient temperature

3: LDA / tetrahydrofuran / 1 h / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; tin(ll) chloride; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)93480-X

Reference yield:

(Z)-2-methyl-5-phenylpent-2-en-4-yn-1-ol (54355-87-2) → (R)-3-((S)-1-Hydroxymethyl-2-methyl-propyl)-5,5-dimethyl-6-((Z)-1-methyl-4-phenyl-but-1-en-3-ynyl)-[1,3]oxazinane-2,4-dione (127743-22-0)

Guidance literature:

Multi-step reaction with 2 steps

1: MnO₂ / CH₂Cl₂; hexane / Ambient temperature

2: 76 percent / SnCl₂, LiAlH₄ / tetrahydrofuran / 18 h / Ambient temperature

With manganese(IV) oxide; lithium aluminium tetrahydride; tin(ll) chloride; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/S0040-4039(01)93480-X

upstream raw materials:

(S)-3-(2-bromo-2-methylpropanoyl)-4-isopropyloxazolidin-2-one

(Z)-2-methyl-5-phenylpent-2-en-4-ynal

(4S)-4-isopropyl-1,3-oxazolidin-2-one

(Z)-2-methyl-5-phenylpent-2-en-4-yn-1-ol

Downstream raw materials:

(Z)-(R)-3-Hydroxy-2,2,4-trimethyl-7-phenyl-hept-4-en-6-ynoic acid methyl ester

(Z)-(R)-3-Hydroxy-2,2,4-trimethyl-7-phenyl-hept-4-en-6-ynoic acid