(R)-2,2-Diethyl-4-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-[1,3]dioxolane

Base Information

• Chemical Name: (R)-2,2-Diethyl-4-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-[1,3]dioxolane
• CAS No.: 203926-58-3
• Molecular Formula: C₁₈H₂₈O₄
• Molecular Weight: 308.418
• Mol file: 203926-58-3.mol

Synonyms:(R)-2,2-Diethyl-4-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-[1,3]dioxolane

Chemical Property of (R)-2,2-Diethyl-4-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-[1,3]dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2,2-Diethyl-4-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-[1,3]dioxolane

There total 1 articles about (R)-2,2-Diethyl-4-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-[1,3]dioxolane 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: 75.0%

p-methoxybenzyl chloride (824-94-2) + (2R,3R)-3,4-diethylmethylenedioxy-2-methyl-butan-1-ol (153185-63-8) → (R)-2,2-Diethyl-4-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-[1,3]dioxolane (203926-58-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;

DOI:10.1021/ja973286p

Reference yield: 80.0%

(R)-2,2-Diethyl-4-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-[1,3]dioxolane (203926-58-3) → (2R,3R)-4-(4-Methoxy-benzyloxy)-3-methyl-butane-1,2-diol (135265-40-6)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.1021/ja973286p

Reference yield:

(R)-2,2-Diethyl-4-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-[1,3]dioxolane (203926-58-3) → okadaic acid (78111-17-8)

Guidance literature:

Multi-step reaction with 21 steps

1: 80 percent / methanolic p-TsOH

2: 87 percent / N-p-toluenesulfonyl imidazole, NaH / tetrahydrofuran

3: 87 percent / BF₃*Et₂O

4: TBAF / tetrahydrofuran

5: Et₃N

6: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 40 min

7: imidazole / CH₂Cl₂ / 0.75 h

8: 1.) CuI / 1.) Et₂O, from -78 to -40 deg C, 2.) Et₂O, -78 deg C, 2.5 h

9: p-TsOH*H₂O / benzene / 11 h / Ambient temperature

10: 98 percent / TBAF / tetrahydrofuran

11: 86 percent / Dess-Martin periodinane

12: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 15 min

13: 1.) NaH

14: n-Bu₃SnH, AIBN / toluene / 2 h / 80 °C

15: 77 percent / aq. Na₂PO₄ buffer, DDQ / CH₂Cl₂; 2-methyl-propan-2-ol / 0.05 h / Irradiation

16: 90 percent / Dess-Marti periodinane, NaHCO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

17: 1.) LiCl, diisopropylethylamine / 1.) CH₃CN, RT, 10 min, 2.) CH₃CN, RT, 20 h

18: (S)-2-methyl-CBS-oxazaborolidine, BF₃*THF / tetrahydrofuran; toluene / 0.08 h / 0 °C

19: p-TsOH*H₂O / benzene / 2 h / Ambient temperature

20: 100 percent / 1M aq. LiOH / tetrahydrofuran / 48 h / Ambient temperature

21: 69 percent / lithium di-tert-butylbiphenylide / tetrahydrofuran / 0.25 h / -78 °C

With 1H-imidazole; lithium hydroxide; copper(l) iodide; n-butyllithium; boron trifluoride-tetrahydrofuran complex; 2,2'-azobis(isobutyronitrile); lithium di-tert-butylbiphenylide; Na₂PO₄ buffer; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; N-tosylimidazole; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol; benzene;

DOI:10.1021/ja973286p

upstream raw materials:

p-methoxybenzyl chloride

(2R,3R)-3,4-diethylmethylenedioxy-2-methyl-butan-1-ol

Downstream raw materials:

(2R,3R)-4-(4-Methoxy-benzyloxy)-3-methyl-butane-1,2-diol

(R)-2-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-oxirane

okadaic acid

tribenzyl okadaic acid

Refernces