(R)-3-{(2R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-propionaldehyde

Base Information

• Chemical Name: (R)-3-{(2R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-propionaldehyde
• CAS No.: 500102-96-5
• Molecular Formula: C₁₉H₂₈O₄
• Molecular Weight: 320.429

Synonyms:(R)-3-{(2R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-propionaldehyde

Chemical Property of (R)-3-{(2R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-propionaldehyde

Chemical Property:

Purity/Quality:

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Technology Process of (R)-3-{(2R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-propionaldehyde

There total 9 articles about (R)-3-{(2R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-propionaldehyde 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: 99.0%

(R)-3-{(2R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-propan-1-ol (500102-77-2) → (R)-3-{(2R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-propionaldehyde (500102-96-5)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane;

DOI:10.1002/1521-3773(20021202)41:23<4560::AID-ANIE4560>3.0.CO;2-B

Reference yield:

(2S,3R)-(+)-2,4-dimethyl-4-pentene-1,3-diol (133005-35-3) → (R)-3-{(2R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-propionaldehyde (500102-96-5)

Guidance literature:

Multi-step reaction with 9 steps

1: imidazole / CH₂Cl₂

2: 52 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂

3: [(cyclopentadienyl)2TiCl₂] / tetrahydrofuran

4: toluene / 110 °C

5: 74 percent / Zn(BH₄)2 / diethyl ether / -78 °C

6: 89 percent / N-iodosuccinimide / acetonitrile / -40 °C

7: 100 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / toluene

8: 95 percent / tetra-(n-butyl)ammonium fluoride / tetrahydrofuran

9: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

With pyridine; 1H-imidazole; dmap; bis(cyclopentadienyl)titanium dichloride; N-iodo-succinimide; zinc(II) tetrahydroborate; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; Dess-Martin periodane; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; 4: Claisen rearrangement;

DOI:10.1002/1521-3773(20021202)41:23<4560::AID-ANIE4560>3.0.CO;2-B

Reference yield:

[[3-(2R,3R)-4R]-3-(3-hydroxy-2,4-dimethyl-1-oxopent-4-enyl)-4-(phenylmethyl)]-2-oxazolidinone (186885-60-9) → (R)-3-{(2R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-propionaldehyde (500102-96-5)

Guidance literature:

Multi-step reaction with 10 steps

1: LiBH₄ / tetrahydrofuran / 0 °C

2: imidazole / CH₂Cl₂

3: 52 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂

4: [(cyclopentadienyl)2TiCl₂] / tetrahydrofuran

5: toluene / 110 °C

6: 74 percent / Zn(BH₄)2 / diethyl ether / -78 °C

7: 89 percent / N-iodosuccinimide / acetonitrile / -40 °C

8: 100 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / toluene

9: 95 percent / tetra-(n-butyl)ammonium fluoride / tetrahydrofuran

10: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

With pyridine; 1H-imidazole; dmap; bis(cyclopentadienyl)titanium dichloride; N-iodo-succinimide; lithium borohydride; zinc(II) tetrahydroborate; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; Dess-Martin periodane; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; 5: Claisen rearrangement;

DOI:10.1002/1521-3773(20021202)41:23<4560::AID-ANIE4560>3.0.CO;2-B

upstream raw materials:

(R)-3-{(2R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-propan-1-ol

(2S,3R)-(+)-2,4-dimethyl-4-pentene-1,3-diol

[[3-(2R,3R)-4R]-3-(3-hydroxy-2,4-dimethyl-1-oxopent-4-enyl)-4-(phenylmethyl)]-2-oxazolidinone

(S)-2-(4-Methoxy-benzyloxy)-propionic acid (R)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-allyl ester

Downstream raw materials:

(S)-1-[(2R,5R)-5-((E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-3-enyl)-5-methyl-tetrahydro-furan-2-yl]-ethanol

1-[(2R,5R)-5-((E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-3-enyl)-5-methyl-tetrahydro-furan-2-yl]-ethanone

(E)-(R)-5-{(2R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2,4-dimethyl-pent-2-en-1-ol

(2R,5R)-2-((E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-3-enyl)-5-[(S)-1-(4-methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan

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