(Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-en-1-ol

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Chemical Name:(Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-en-1-ol
CAS No.:259199-03-6
Molecular Formula:C₂₁H₃₀O₄
Molecular Weight:346.467
Hs Code.:

Synonyms:(Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-en-1-ol

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Chemical Property of (Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-en-1-ol

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Technology Process of (Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-en-1-ol

There total 9 articles about (Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-en-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: 86.0%

: 259199-02-5
(Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

: 259199-03-6
(Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1016/S0040-4039(99)02021-3

Reference yield:

: 136320-64-4
(2R)-3-[(4-methoxybenzyl)oxy]-2-methylpropanol

: 259199-03-6
(Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine / 20 °C

2: dimethylsulfoxide / 80 °C

3: 80 percent / DIBAH / tetrahydrofuran / -78 - 20 °C

4: 90 percent / diethyl ether / -100 °C

5: 84 percent / PPTS / toluene / 35 °C / 60 Torr

6: 94 percent / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / Heating

7: 81 percent / montmorillonite K-10 / CH₂Cl₂ / 20 °C

8: 73 percent / KHMDS; 18-crown-6 / tetrahydrofuran / -78 °C

9: 86 percent / DIBAH / tetrahydrofuran / -78 - 20 °C

With pyridine; Grubbs catalyst first generation; 18-crown-6 ether; montmorillonite K-10; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; 1: Tosylation / 2: Substitution / 3: Reduction / 4: modified Brown allylation / 5: transketalization / 6: Cyclization / 7: Alkylation / 8: Alkylation / 9: Reduction;
DOI:10.1016/S0040-4039(99)02021-3

Reference yield:

: 259198-97-5
(3R)-4-(4-methoxybenzyloxy)-3-methylbutyraldehyde

: 259199-03-6
(Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / diethyl ether / -100 °C

2: 84 percent / PPTS / toluene / 35 °C / 60 Torr

3: 94 percent / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / Heating

4: 81 percent / montmorillonite K-10 / CH₂Cl₂ / 20 °C

5: 73 percent / KHMDS; 18-crown-6 / tetrahydrofuran / -78 °C

6: 86 percent / DIBAH / tetrahydrofuran / -78 - 20 °C

With Grubbs catalyst first generation; 18-crown-6 ether; montmorillonite K-10; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1: modified Brown allylation / 2: transketalization / 3: Cyclization / 4: Alkylation / 5: Alkylation / 6: Reduction;
DOI:10.1016/S0040-4039(99)02021-3