(5R)-5-<(1R)-2-<(tert-butyldimethylsilyl)oxy>-1-hydroxyethyl>-5-<2-(tetradecanoxycarbonyl)-(E)-ethenyl>tetrahydro-2-furanone

Base Information

• Chemical Name: (5R)-5-<(1R)-2-<(tert-butyldimethylsilyl)oxy>-1-hydroxyethyl>-5-<2-(tetradecanoxycarbonyl)-(E)-ethenyl>tetrahydro-2-furanone
• CAS No.: 172751-35-8
• Molecular Formula: C₃₉H₅₈O₆Si
• Molecular Weight: 650.971
• Mol file: 172751-35-8.mol

Synonyms:

Chemical Property of (5R)-5-<(1R)-2-<(tert-butyldimethylsilyl)oxy>-1-hydroxyethyl>-5-<2-(tetradecanoxycarbonyl)-(E)-ethenyl>tetrahydro-2-furanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-5-<(1R)-2-<(tert-butyldimethylsilyl)oxy>-1-hydroxyethyl>-5-<2-(tetradecanoxycarbonyl)-(E)-ethenyl>tetrahydro-2-furanone

There total 4 articles about (5R)-5-<(1R)-2-<(tert-butyldimethylsilyl)oxy>-1-hydroxyethyl>-5-<2-(tetradecanoxycarbonyl)-(E)-ethenyl>tetrahydro-2-furanone 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:

5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose (172751-32-5) → (5R)-5-<(1R)-2-<(tert-butyldimethylsilyl)oxy>-1-hydroxyethyl>-5-<2-(tetradecanoxycarbonyl)-(E)-ethenyl>tetrahydro-2-furanone (172751-35-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) MeMgCl, 2.) Mg, dibromoethane

2: 85.7 percent / pyridinium chlorochromate, 4A molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

3: 68 percent / 1 N aq. HCl / tetrahydrofuran / 11 h / Ambient temperature

4: aq. NaIO₄ / methanol / 3.5 h / Ambient temperature

5: benzene / 18 h / Ambient temperature

With hydrogenchloride; sodium periodate; 1,1-Dibromoethane; 4 A molecular sieve; methylmagnesium chloride; magnesium; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jm950278f

Reference yield:

(5R,6R,9S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-8,9-dihydroxy-1,7-dioxa-spiro[4.4]nonan-2-one → (5R)-5-<(1R)-2-<(tert-butyldimethylsilyl)oxy>-1-hydroxyethyl>-5-<2-(tetradecanoxycarbonyl)-(E)-ethenyl>tetrahydro-2-furanone (172751-35-8)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaIO₄ / methanol / 3.5 h / Ambient temperature

2: benzene / 18 h / Ambient temperature

With sodium periodate; In methanol; benzene;

DOI:10.1021/jm950278f

Reference yield:

5-O-(tert-butyldiphenylsilyl)-3-C-(3-hydroxypropyl)-1,2-O-isopropylidene-β-D-lyxofuranose (172751-33-6) → (5R)-5-<(1R)-2-<(tert-butyldimethylsilyl)oxy>-1-hydroxyethyl>-5-<2-(tetradecanoxycarbonyl)-(E)-ethenyl>tetrahydro-2-furanone (172751-35-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 85.7 percent / pyridinium chlorochromate, 4A molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

2: 68 percent / 1 N aq. HCl / tetrahydrofuran / 11 h / Ambient temperature

3: aq. NaIO₄ / methanol / 3.5 h / Ambient temperature

4: benzene / 18 h / Ambient temperature

With hydrogenchloride; sodium periodate; 4 A molecular sieve; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jm950278f

upstream raw materials:

5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose

5-O-(tert-butyldiphenylsilyl)-3-C-(3-hydroxypropyl)-1,2-O-isopropylidene-β-D-lyxofuranose

(5S,6R,8S,9S)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-8,9-O-isopropylidene-2-keto-1,7-dioxaspiro<4.4>nonane