(2S,3S,4R,5R)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)-5-(triisopropylsiloxymethyl)oxolane

Base Information

• Chemical Name: (2S,3S,4R,5R)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)-5-(triisopropylsiloxymethyl)oxolane
• CAS No.: 164364-99-2
• Molecular Formula: C₂₇H₄₆O₅Si
• Molecular Weight: 478.745
• Mol file: 164364-99-2.mol

Synonyms:(2S,3S,4R,5R)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)-5-(triisopropylsiloxymethyl)oxolane

Chemical Property of (2S,3S,4R,5R)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)-5-(triisopropylsiloxymethyl)oxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)-5-(triisopropylsiloxymethyl)oxolane

There total 14 articles about (2S,3S,4R,5R)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)-5-(triisopropylsiloxymethyl)oxolane 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: 98.0%

triisopropylsilyl chloride (13154-24-0) + (2S,3S,4R,5R)-5-(hydroxymethyl)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)oxolane (536737-61-8) → (2S,3S,4R,5R)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)-5-(triisopropylsiloxymethyl)oxolane (164364-99-2)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 20 ℃;

DOI:10.1021/ja034332q

Reference yield:

(S,E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropionic acid ethyl ester (81997-76-4) → (2S,3S,4R,5R)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)-5-(triisopropylsiloxymethyl)oxolane (164364-99-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 85 percent / aq. HCl / tetrahydrofuran

2: 90 percent / DIBAL / -78 °C

3: 80 percent / (+)-DIPT; Ti(O-i-Pr)4; TBHP / MS 4 Angstroem / CH₂Cl₂ / 6 h / -20 °C

4: TPAP; NMO; MS 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

5: 837 mg / tetrahydrofuran / 0.5 h / -20 °C

6: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

7: 93 percent / TiCl₄ / CH₂Cl₂ / 0.33 h / -78 °C

8: 82 percent / HCl; ethylene glycol / diethyl ether; tetrahydrofuran

9: 82 percent / KH / tetrahydrofuran / 2 h / Heating

10: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

11: 84 percent / HCl / diethyl ether / 2 h / 20 °C

12: 98 percent / DMAP; imidazole / CH₂Cl₂ / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; L-(+)-diisopropyl tartrate; MS 4 Angstroem; tetrabutyl ammonium fluoride; titanium tetrachloride; potassium hydride; diisobutylaluminium hydride; ethylene glycol; MS 4 Angstroem; In tetrahydrofuran; diethyl ether; dichloromethane; 5: Sharpless asymmetric epoxidation / 9: Tsuchihashi-Suzuki rearrangement;

DOI:10.1021/ja034332q

Reference yield:

(E)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-5-triisopropylsilanyloxy-pent-2-en-1-ol (164364-94-7) → (2S,3S,4R,5R)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)-5-(triisopropylsiloxymethyl)oxolane (164364-99-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 80 percent / (+)-DIPT; Ti(O-i-Pr)4; TBHP / MS 4 Angstroem / CH₂Cl₂ / 6 h / -20 °C

2: TPAP; NMO; MS 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

3: 837 mg / tetrahydrofuran / 0.5 h / -20 °C

4: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

5: 93 percent / TiCl₄ / CH₂Cl₂ / 0.33 h / -78 °C

6: 82 percent / HCl; ethylene glycol / diethyl ether; tetrahydrofuran

7: 82 percent / KH / tetrahydrofuran / 2 h / Heating

8: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

9: 84 percent / HCl / diethyl ether / 2 h / 20 °C

10: 98 percent / DMAP; imidazole / CH₂Cl₂ / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; L-(+)-diisopropyl tartrate; MS 4 Angstroem; tetrabutyl ammonium fluoride; titanium tetrachloride; potassium hydride; ethylene glycol; MS 4 Angstroem; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Sharpless asymmetric epoxidation / 5: Tsuchihashi-Suzuki rearrangement;

DOI:10.1021/ja034332q

upstream raw materials:

triisopropylsilyl chloride

(2S,3S,4R,5R)-5-(hydroxymethyl)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyl-3-(2-propenyl)oxolane

(S,E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropionic acid ethyl ester

(E)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-5-triisopropylsilanyloxy-pent-2-en-1-ol

Downstream raw materials:

(R)-2-[(3R,4R,5R)-2-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-furan-3-yl]-propane-1,2-diol