(2S,3S)-2-Allyl-3-hydroxy-4,4-dimethyl-1-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-heptane-1,5-dione

Base Information

• Chemical Name: (2S,3S)-2-Allyl-3-hydroxy-4,4-dimethyl-1-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-heptane-1,5-dione
• CAS No.: 245040-40-8
• Molecular Formula: C₂₂H₂₉NO₅
• Molecular Weight: 387.476
• Mol file: 245040-40-8.mol

Synonyms:(2S,3S)-2-Allyl-3-hydroxy-4,4-dimethyl-1-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-heptane-1,5-dione

Chemical Property of (2S,3S)-2-Allyl-3-hydroxy-4,4-dimethyl-1-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-heptane-1,5-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-Allyl-3-hydroxy-4,4-dimethyl-1-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-heptane-1,5-dione

There total 1 articles about (2S,3S)-2-Allyl-3-hydroxy-4,4-dimethyl-1-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-heptane-1,5-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: 49.0%

(4S,5R)-4-Methyl-3-(pent-4-enoyl)-5-phenyl-1,3-oxazolidin-2-one (128461-58-5) + 2,2-dimethyl-3-oxopentanal (106921-60-2) → (2R,3R)-2-Allyl-3-hydroxy-4,4-dimethyl-1-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-heptane-1,5-dione + (2S,3S)-2-Allyl-3-hydroxy-4,4-dimethyl-1-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-heptane-1,5-dione (245040-40-8)

Guidance literature:

(4S,5R)-4-Methyl-3-(pent-4-enoyl)-5-phenyl-1,3-oxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 0 ℃;

2,2-dimethyl-3-oxopentanal; In dichloromethane; at -78 - 0 ℃; for 3h;

DOI:10.1016/S0040-4020(99)00301-4

Reference yield:

(2S,3S)-2-Allyl-3-hydroxy-4,4-dimethyl-1-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-heptane-1,5-dione (245040-40-8) → (Z)-(4aR,9S,10S,11R,13aS)-10-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-9,11,13,13-tetramethyl-4a,5,8,9,10,11,13,13a-octahydro-4H-1,3-dioxa-benzocycloundecen-12-one

Guidance literature:

Multi-step reaction with 5 steps

1.1: 63 percent / LiBH₄; H₂O / diethyl ether; tetrahydrofuran / 4 h / 0 - 25 °C

2.1: camphosulfonic acid / CH₂Cl₂ / 1 h / -78 °C

2.2: 55 percent / Dess-Martin periodinane reagent / CH₂Cl₂ / 2 h / 0 - 25 °C

3.1: 62 percent / iPr₂NH; nBuLi / tetrahydrofuran / 0.33 h / -78 °C

4.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 - 25 °C

5.1: 74 percent / Ti(OiPr)4 / bis(tricyclohexyl-phosphine)benzylideneruthenium dichloride / CH₂Cl₂ / 7 h / Heating

With 2,6-dimethylpyridine; titanium(IV) isopropylate; lithium borohydride; n-butyllithium; camphor-10-sulfonic acid; water; diisopropylamine; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Reduction / 2.1: Condensation / 2.2: Oxidation / 3.1: Condensation / 4.1: Silylation / 5.1: olefin metathesis;

DOI:10.1016/S0040-4020(99)00301-4

Reference yield:

(2S,3S)-2-Allyl-3-hydroxy-4,4-dimethyl-1-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-heptane-1,5-dione (245040-40-8) → 4-Bromo-benzoic acid (1R,2S,5R,6S,7S)-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3,3,5,7-tetramethyl-4-oxo-cycloundecylmethyl ester

Guidance literature:

Multi-step reaction with 8 steps

1.1: 63 percent / LiBH₄; H₂O / diethyl ether; tetrahydrofuran / 4 h / 0 - 25 °C

2.1: camphosulfonic acid / CH₂Cl₂ / 1 h / -78 °C

2.2: 55 percent / Dess-Martin periodinane reagent / CH₂Cl₂ / 2 h / 0 - 25 °C

3.1: 62 percent / iPr₂NH; nBuLi / tetrahydrofuran / 0.33 h / -78 °C

4.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 - 25 °C

5.1: 74 percent / Ti(OiPr)4 / bis(tricyclohexyl-phosphine)benzylideneruthenium dichloride / CH₂Cl₂ / 7 h / Heating

6.1: HCl/MeOH / diethyl ether / 0.42 h

7.1: H₂ / Pd/C / methanol; ethyl acetate / 18 h / 760 Torr

8.1: 24 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 0 - 25 °C

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; methanol; dmap; lithium borohydride; n-butyllithium; camphor-10-sulfonic acid; water; hydrogen; diisopropylamine; palladium on activated charcoal; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; 1.1: Reduction / 2.1: Condensation / 2.2: Oxidation / 3.1: Condensation / 4.1: Silylation / 5.1: olefin metathesis / 6.1: Hydrolysis / 7.1: Catalytic hydrogenation / 8.1: Esterification;

DOI:10.1016/S0040-4020(99)00301-4

upstream raw materials:

(4S,5R)-4-Methyl-3-(pent-4-enoyl)-5-phenyl-1,3-oxazolidin-2-one

2,2-dimethyl-3-oxopentanal

Downstream raw materials:

2-[(4S,5R)-5-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2-methyl-pentan-3-one

(4R,5S,6S)-2-[(4S,5R)-5-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-5-hydroxy-2,4,6-trimethyl-non-8-en-3-one

(4R,5S,6S)-2-[(4S,5R)-5-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-8-en-3-one