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

Base Information

• Chemical Name: (R)-3-{(2R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-propan-1-ol
• CAS No.: 500102-77-2
• Molecular Formula: C₁₉H₃₀O₄
• Molecular Weight: 322.445

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

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

Chemical Property:

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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-propan-1-ol

There total 8 articles about (R)-3-{(2R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-propan-1-ol 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: 95.0%

tert-Butyl-((R)-3-{(R)-5-[(S)-1-(4-methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-propoxy)-dimethyl-silane → (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)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

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-propan-1-ol (500102-77-2)

Guidance literature:

Multi-step reaction with 8 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

With 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; 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-propan-1-ol (500102-77-2)

Guidance literature:

Multi-step reaction with 9 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

With 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; 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:

(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

(E)-(2S,8R)-9-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-6,8-dimethyl-non-6-en-3-one

Downstream raw materials:

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

(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

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