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

Base Information

• Chemical Name: 3-{(4R,5R)-5-[(E)-4-(4-Methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl}-propan-1-ol
• CAS No.: 264921-01-9
• Molecular Formula: C₂₁H₃₂O₄
• Molecular Weight: 348.483
• Mol file: 264921-01-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{(4R,5R)-5-[(E)-4-(4-Methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl}-propan-1-ol

There total 11 articles about 3-{(4R,5R)-5-[(E)-4-(4-Methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl}-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: 72.0%

(2R,3R)-5-Allyl-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan (264921-00-8) → 3-{(4R,5R)-5-[(E)-4-(4-Methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl}-propan-1-ol (264921-01-9)

Guidance literature:

(2R,3R)-5-Allyl-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 0 ℃; for 24h;

With sodium hydroxide; dihydrogen peroxide; Further stages.;

DOI:10.1021/ol005510c

Reference yield:

(E)-5-(4-methoxyphenylmethyloxy)-2-methyl-2-pentenal (110597-90-5) → 3-{(4R,5R)-5-[(E)-4-(4-Methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl}-propan-1-ol (264921-01-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 68 percent / Bu₂BOTf; i-Pr₂NEt / diethyl ether / 6 h / -78 °C

2.1: 80 percent / MeOH / 2 h / -78 - -10 °C

3.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / -78 °C

4.1: 93 percent / DIBAl-H / CH₂Cl₂ / 0.5 h / -78 °C

5.1: 99 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 °C

6.1: 97 percent / KO-t-Bu / tetrahydrofuran / 2 h / 0 - 22 °C

7.1: 86 percent / p-TsOH / tetrahydrofuran; H₂O / 25 °C

8.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 22 °C

9.1: 95 percent / BF₃*OEt₂ / diethyl ether / -78 °C

10.1: 9-BBN / tetrahydrofuran / 24 h / 0 °C

10.2: 72 percent / H₂O₂; NaOH

With 2,6-dimethylpyridine; methanol; dmap; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; potassium tert-butylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; 1.1: Heathcock anti-aldol reaction / 2.1: methanolysis / 3.1: silylation / 4.1: Reduction / 5.1: Swern oxidation / 6.1: Wittig reaction / 7.1: Cyclization / 8.1: Acetylation / 9.1: allylation / 10.1: hydroboration / 10.2: Oxidation;

DOI:10.1021/ol005510c

Reference yield:

(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoic acid methyl ester (264920-93-6) → 3-{(4R,5R)-5-[(E)-4-(4-Methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl}-propan-1-ol (264921-01-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / -78 °C

2.1: 93 percent / DIBAl-H / CH₂Cl₂ / 0.5 h / -78 °C

3.1: 99 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 °C

4.1: 97 percent / KO-t-Bu / tetrahydrofuran / 2 h / 0 - 22 °C

5.1: 86 percent / p-TsOH / tetrahydrofuran; H₂O / 25 °C

6.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 22 °C

7.1: 95 percent / BF₃*OEt₂ / diethyl ether / -78 °C

8.1: 9-BBN / tetrahydrofuran / 24 h / 0 °C

8.2: 72 percent / H₂O₂; NaOH

With 2,6-dimethylpyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; 1.1: silylation / 2.1: Reduction / 3.1: Swern oxidation / 4.1: Wittig reaction / 5.1: Cyclization / 6.1: Acetylation / 7.1: allylation / 8.1: hydroboration / 8.2: Oxidation;

DOI:10.1021/ol005510c

upstream raw materials:

(2R,3R)-5-Allyl-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan

(E)-5-(4-methoxyphenylmethyloxy)-2-methyl-2-pentenal

(4R,5R)-5-[(E)-4-(4-Methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-ol

(2R,3R)-5-Methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan