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

Base Information

• Chemical Name: (2R,3R)-5-Allyl-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan
• CAS No.: 264921-00-8
• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.467
• Mol file: 264921-00-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (2R,3R)-5-Allyl-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan 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%

(2R,3R)-5-Methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan (264920-97-0) + allyl-trimethyl-silane (762-72-1) → (2R,3R)-5-Allyl-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan (264921-00-8)

Guidance literature:

With boron trifluoride diethyl etherate; In diethyl ether; at 0 ℃; for 3h;

DOI:10.1021/ol005510c

Reference yield: 95.0%

Acetic acid (4R,5R)-5-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl ester (264920-99-2) + allyl-trimethyl-silane (762-72-1) → (2R,3R)-5-Allyl-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan (264921-00-8)

Guidance literature:

With boron trifluoride diethyl etherate; In diethyl ether; at -78 ℃;

DOI:10.1021/ol005510c

Reference yield:

(E)-5-(4-methoxyphenylmethyloxy)-2-methyl-2-pentenal (110597-90-5) → (2R,3R)-5-Allyl-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan (264921-00-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 68 percent / Bu₂BOTf; i-Pr₂NEt / diethyl ether / 6 h / -78 °C

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

3: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / -78 °C

4: 93 percent / DIBAl-H / CH₂Cl₂ / 0.5 h / -78 °C

5: 99 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 °C

6: 97 percent / KO-t-Bu / tetrahydrofuran / 2 h / 0 - 22 °C

7: 86 percent / p-TsOH / tetrahydrofuran; H₂O / 25 °C

8: Et₃N; DMAP / CH₂Cl₂ / 2 h / 22 °C

9: 95 percent / BF₃*OEt₂ / diethyl ether / -78 °C

With 2,6-dimethylpyridine; methanol; dmap; 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: Heathcock anti-aldol reaction / 2: methanolysis / 3: silylation / 4: Reduction / 5: Swern oxidation / 6: Wittig reaction / 7: Cyclization / 8: Acetylation / 9: allylation;

DOI:10.1021/ol005510c

upstream raw materials:

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

allyl-trimethyl-silane

Acetic acid (4R,5R)-5-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl ester

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

Downstream raw materials:

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