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

Base Information

Chemical Name:(2R,3R)-5-Methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan
CAS No.:264920-97-0
Molecular Formula:C₁₉H₂₈O₄
Molecular Weight:320.429
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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

There total 7 articles about (2R,3R)-5-Methoxy-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: 86.0%

: 264920-96-9
Triethyl-[(E)-(R)-5-(4-methoxy-benzyloxy)-1-((E)-(R)-3-methoxy-1-methyl-allyl)-2-methyl-pent-2-enyloxy]-silane

: 264920-97-0
(2R,3R)-5-Methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 22 ℃; for 0.5h;
DOI:10.1021/ol005510c

Reference yield:

: 110597-90-5
(E)-5-(4-methoxyphenylmethyloxy)-2-methyl-2-pentenal

: 264920-97-0
(2R,3R)-5-Methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan

Guidance literature:: Multi-step reaction with 7 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 / methanol / 0.5 h / 22 °C

With 2,6-dimethylpyridine; methanol; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1: Heathcock anti-aldol reaction / 2: methanolysis / 3: silylation / 4: Reduction / 5: Swern oxidation / 6: Wittig reaction / 7: Cyclization;
DOI:10.1021/ol005510c

Reference yield:

: 264920-93-6
(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoic acid methyl ester

: 264920-97-0
(2R,3R)-5-Methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / -78 °C

2: 93 percent / DIBAl-H / CH₂Cl₂ / 0.5 h / -78 °C

3: 99 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 °C

4: 97 percent / KO-t-Bu / tetrahydrofuran / 2 h / 0 - 22 °C

5: 86 percent / p-TsOH / methanol / 0.5 h / 22 °C

With 2,6-dimethylpyridine; oxalyl dichloride; potassium tert-butylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1: silylation / 2: Reduction / 3: Swern oxidation / 4: Wittig reaction / 5: Cyclization;
DOI:10.1021/ol005510c