3-((2S,5S)-3-methylene-5-(3-(t-butyldiphenylsilyloxy)propyl)tetrahydrofuran-2-yl)propanal

Base Information

• Chemical Name: 3-((2S,5S)-3-methylene-5-(3-(t-butyldiphenylsilyloxy)propyl)tetrahydrofuran-2-yl)propanal
• CAS No.: 481048-34-4
• Molecular Formula: C₂₇H₃₆O₃Si
• Molecular Weight: 436.667
• Mol file: 481048-34-4.mol

Synonyms:3-((2S,5S)-3-methylene-5-(3-(t-butyldiphenylsilyloxy)propyl)tetrahydrofuran-2-yl)propanal

Chemical Property of 3-((2S,5S)-3-methylene-5-(3-(t-butyldiphenylsilyloxy)propyl)tetrahydrofuran-2-yl)propanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((2S,5S)-3-methylene-5-(3-(t-butyldiphenylsilyloxy)propyl)tetrahydrofuran-2-yl)propanal

There total 13 articles about 3-((2S,5S)-3-methylene-5-(3-(t-butyldiphenylsilyloxy)propyl)tetrahydrofuran-2-yl)propanal 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: 96.4%

3-((2S,5S)-3-methylene-5-(3-(t-butyldiphenylsilyloxy)propyl)tetrahydrofuran-2-yl)propanol (481048-21-9) → 3-((2S,5S)-3-methylene-5-(3-(t-butyldiphenylsilyloxy)propyl)tetrahydrofuran-2-yl)propanal (481048-34-4)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

Reference yield:

toluene-4-sulfonic acid 3-bromo-1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-but-3-enyl ester (871355-80-5) → 3-((2S,5S)-3-methylene-5-(3-(t-butyldiphenylsilyloxy)propyl)tetrahydrofuran-2-yl)propanal (481048-34-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiCl; Et₃N*HCl; Ni(COD)2 / Mn/(S)-chiral Cr(III) sulfonamide complex; TMS-Cl / various solvent(s) / 24 h / 20 °C

1.2: 80 percent / PPTS; Py / propan-2-ol / 24 h / 20 °C

2.1: 84 percent / K₂CO₃ / methanol / 20 h / 20 °C

3.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; triethylamine hydrochloride; potassium carbonate; Dess-Martin periodane; lithium chloride; manganese; chloro-trimethyl-silane; (S)-chiral Cr(III) sulfonamide; In methanol; dichloromethane; 3.1: Dess-Martin oxidation;

DOI:10.1021/ol026981x

Reference yield:

toluene-4-sulfonic acid 1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-iodo-but-3-enyl ester → 3-((2S,5S)-3-methylene-5-(3-(t-butyldiphenylsilyloxy)propyl)tetrahydrofuran-2-yl)propanal (481048-34-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiCl; (Bn)(n-Bu)3NCl; NiCl₂ / Mn/(S)-chiral Cr(III) sulfonamide complex; TMS-Cl / tetrahydrofuran / 12 h / 20 °C

1.2: 72 percent / PPTS; Py / propan-2-ol / 24 h / 20 °C

2.1: 84 percent / K₂CO₃ / methanol / 20 h / 20 °C

3.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With benzyltri(n-butyl)ammonium chloride; potassium carbonate; Dess-Martin periodane; lithium chloride; nickel dichloride; manganese; chloro-trimethyl-silane; (S)-chiral Cr(III) sulfonamide; In tetrahydrofuran; methanol; dichloromethane; 3.1: Dess-Martin oxidation;

DOI:10.1021/ol026981x

upstream raw materials:

3-((2S,5S)-3-methylene-5-(3-(t-butyldiphenylsilyloxy)propyl)tetrahydrofuran-2-yl)propanol

toluene-4-sulfonic acid 3-bromo-1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-but-3-enyl ester

methanesulfonic acid 1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-iodo-but-3-enyl ester

(S)-7-((tert-butyldiphenylsilyl)oxy)hept-1-yn-4-ol

Downstream raw materials:

3-((2S,5S)-5-((3R,5R)-3-hydroxy-6-iodo-5-methylhept-6-en-1-yl)-4-methylenetetrahydrofuran-2-yl)propyl pivalate