[2R,6R]-6-[(2R)-(4-benzenesulfonyl-2-methylbutyl)-5,6-dihydro-2H-pyran-2-yl]acetaldehyde

Base Information

• Chemical Name: [2R,6R]-6-[(2R)-(4-benzenesulfonyl-2-methylbutyl)-5,6-dihydro-2H-pyran-2-yl]acetaldehyde
• CAS No.: 385809-12-1
• Molecular Formula: C₁₈H₂₄O₄S
• Molecular Weight: 336.452

Synonyms:[2R,6R]-6-[(2R)-(4-benzenesulfonyl-2-methylbutyl)-5,6-dihydro-2H-pyran-2-yl]acetaldehyde

Chemical Property of [2R,6R]-6-[(2R)-(4-benzenesulfonyl-2-methylbutyl)-5,6-dihydro-2H-pyran-2-yl]acetaldehyde

Chemical Property:

Purity/Quality:

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Technology Process of [2R,6R]-6-[(2R)-(4-benzenesulfonyl-2-methylbutyl)-5,6-dihydro-2H-pyran-2-yl]acetaldehyde

There total 21 articles about [2R,6R]-6-[(2R)-(4-benzenesulfonyl-2-methylbutyl)-5,6-dihydro-2H-pyran-2-yl]acetaldehyde 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: 82.0%

tert-butyldimethylsilyl vinyl ether (66031-93-4) + [2R,6S]-2-[(2R)-4-benzenesulfonyl-2-methylbutyl]-6-ethoxy-3,6-dihydro-2H-pyran (527742-75-2) → [2R,6R]-6-[(2R)-(4-benzenesulfonyl-2-methylbutyl)-5,6-dihydro-2H-pyran-2-yl]acetaldehyde (385809-12-1) + [2S,6R]-6-[(2R)-(4-benzenesulfonyl-2-methylbutyl)-5,6-dihydro-2H-pyran-2-yl]acetaldehyde

Guidance literature:

tert-butyldimethylsilyl vinyl ether; [2R,6S]-2-[(2R)-4-benzenesulfonyl-2-methylbutyl]-6-ethoxy-3,6-dihydro-2H-pyran; With Montmorillonite K₁₀ clay; In dichloromethane; at 0 - 5 ℃; for 0.666667h;

With Montmorillonite K₁₀ clay; In dichloromethane; water; at 20 ℃; for 0.5h;

DOI:10.1021/jo026743f

Reference yield:

(6S)-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydro-2H-pyran-2-one (527742-73-0) → [2R,6R]-6-[(2R)-(4-benzenesulfonyl-2-methylbutyl)-5,6-dihydro-2H-pyran-2-yl]acetaldehyde (385809-12-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: CuI / 0 °C

1.2: 84 percent / diethyl ether / 1 h / 0 °C

2.1: 98 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

3.1: 83 percent / Bu₃P / tetrahydrofuran / 16 h / 0 - 20 °C

4.1: Et₃N / CH₂Cl₂ / 1 h / -10 °C

5.1: TBAF / tetrahydrofuran / 1 h / 0 - 5 °C

5.2: 812 mg / aq. NaOH / tetrahydrofuran / 0.75 h / 0 - 5 °C

6.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 1.5 h / -78 °C

6.2: aq. TFA / 3 h / 20 °C

6.3: 88 percent / DBU / CH₂Cl₂ / 0.5 h / 0 - 5 °C

7.1: 100 percent / magnesium monoperoxophthalate hexahydrate / ethanol / 1.5 h / 20 °C

8.1: DIBALH / CH₂Cl₂ / 1 h / -78 °C

9.1: 1.107 g / PPTS / 20 °C

10.1: montmorillonite K₁₀ clay / CH₂Cl₂ / 0.67 h / 0 - 5 °C

10.2: 82 percent / montmorillonite K₁₀ clay / CH₂Cl₂; H₂O / 0.5 h / 20 °C

With copper(l) iodide; lithium borohydride; n-butyllithium; magnesium bis(monoperoxyphthalate)hexahydrate; tributylphosphine; Montmorillonite K₁₀ clay; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1021/jo026743f

Reference yield:

[3S,5S]-6-(tert-butyldimethylsilanyloxy)-3-methylhexane-1,5-diol (527742-74-1) → [2R,6R]-6-[(2R)-(4-benzenesulfonyl-2-methylbutyl)-5,6-dihydro-2H-pyran-2-yl]acetaldehyde (385809-12-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 83 percent / Bu₃P / tetrahydrofuran / 16 h / 0 - 20 °C

2.1: Et₃N / CH₂Cl₂ / 1 h / -10 °C

3.1: TBAF / tetrahydrofuran / 1 h / 0 - 5 °C

3.2: 812 mg / aq. NaOH / tetrahydrofuran / 0.75 h / 0 - 5 °C

4.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 1.5 h / -78 °C

4.2: aq. TFA / 3 h / 20 °C

4.3: 88 percent / DBU / CH₂Cl₂ / 0.5 h / 0 - 5 °C

5.1: 100 percent / magnesium monoperoxophthalate hexahydrate / ethanol / 1.5 h / 20 °C

6.1: DIBALH / CH₂Cl₂ / 1 h / -78 °C

7.1: 1.107 g / PPTS / 20 °C

8.1: montmorillonite K₁₀ clay / CH₂Cl₂ / 0.67 h / 0 - 5 °C

8.2: 82 percent / montmorillonite K₁₀ clay / CH₂Cl₂; H₂O / 0.5 h / 20 °C

With n-butyllithium; magnesium bis(monoperoxyphthalate)hexahydrate; tributylphosphine; Montmorillonite K₁₀ clay; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1021/jo026743f

upstream raw materials:

tert-butyldimethylsilyl vinyl ether

(R)-2-((R)-4-Benzenesulfonyl-2-methyl-butyl)-6-ethoxy-3,6-dihydro-2H-pyran

[2R,6S]-2-[(2R)-4-benzenesulfonyl-2-methylbutyl]-6-ethoxy-3,6-dihydro-2H-pyran

(5S,6R)-5-acetoxy-6-(acetoxymethyl)-5,6-dihydro-2H-pyran-2-one

Downstream raw materials:

[2R,6R]-6-[(2R)-(4-benzenesulfonyl-2-methylbutyl)-5,6-dihydro-2H-pyran-2-yl]ethanol

(2R,6R)-tert-butyl-[2-(6-{4-[(2S)-3-(4-methoxybenzyloxy)-2-methoxymethoxy-propyl]-[(2S)-2-methylpent-4-enyl]}-5,6-dihydro-2H-pyran-2-yl)-ethoxy]-dimethylsilane

[2R,(2R),6R]-{2-[6-(4-benzenesulfonyl-2-methylbutyl)-5,6-dihydro-2H-pyran-2-yl]ethoxy}-tert-butyldimethylsilane

(2S,4RS,6R)-4-benzenesulfonyl-7-{(2R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-1-(4-methoxybenzyloxy)-6-methylheptan-2-ol

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