(-)-(4R,5S)-5-((1'S)-hydroxypropyl)-4-(phenyldimethylsilyl)-dihydrofuran-2-one

Base Information

• Chemical Name: (-)-(4R,5S)-5-((1'S)-hydroxypropyl)-4-(phenyldimethylsilyl)-dihydrofuran-2-one
• CAS No.: 142730-72-1
• Molecular Formula: C₁₅H₂₂O₃Si
• Molecular Weight: 278.423
• Mol file: 142730-72-1.mol

Synonyms:(-)-(4R,5S)-5-((1'S)-hydroxypropyl)-4-(phenyldimethylsilyl)-dihydrofuran-2-one

Chemical Property of (-)-(4R,5S)-5-((1'S)-hydroxypropyl)-4-(phenyldimethylsilyl)-dihydrofuran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(4R,5S)-5-((1'S)-hydroxypropyl)-4-(phenyldimethylsilyl)-dihydrofuran-2-one

There total 5 articles about (-)-(4R,5S)-5-((1'S)-hydroxypropyl)-4-(phenyldimethylsilyl)-dihydrofuran-2-one 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:

(+)-methyl (R)-E-3-(phenyldimethylsilyl)hept-4-enoate (142730-71-0) → (+)-(4R,5R)-5-((1'R)-hydroxypropyl)-4-(phenyldimethylsilyl)-dihydrofuran-2-one (142730-73-2) + (-)-(4R,5S)-5-((1'S)-hydroxypropyl)-4-(phenyldimethylsilyl)-dihydrofuran-2-one (142730-72-1)

Guidance literature:

With osmium(VIII) oxide; potassium carbonate; potassium hexacyanoferrate(III); dihydroquinine 4-chlorobenzoate; In water; tert-butyl alcohol; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)92089-6

Reference yield:

pent-1-yn-3-ol (4187-86-4) → (-)-(4R,5S)-5-((1'S)-hydroxypropyl)-4-(phenyldimethylsilyl)-dihydrofuran-2-one (142730-72-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / bis(2,5-norbornene)tris(tert-butyl)phosphine-platinum⁽⁰⁾ / tetrahydrofuran / 18 h / Heating

2: 1.) titanium tetraisopropoxide, L-(+)-diethyl tartrate, 4 A molecular sieves, 2.) 5.48 M tert-butylhydroperoxide, 3.) dimethyl sulphide / 1.) CH₂Cl₂, 20 min, 2.) CH₂Cl₂, -20 deg C, 48 h, 3.) CH₂Cl₂, 1 h

3: 93 percent / propionic acid / toluene / 30 min, reflux, addition repeated 3 times

4: 2 percent w/v OsO₄, K₃Fe(CN)6, K₂CO₃, dihyroquinidine 4-chlorobenzoate / 2-methyl-propan-2-ol; H₂O / 18 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; osmium(VIII) oxide; dimethylsulfide; diethyl (2R,3R)-tartrate; dihydroquinidine 9-O-(4-chlorobenzoate); 4 A molecular sieve; potassium carbonate; propionic acid; potassium hexacyanoferrate(III); bis(2,5-norbornene)tris(tert-butyl)phosphine-platinum⁽⁰⁾; In tetrahydrofuran; water; toluene; tert-butyl alcohol;

DOI:10.1016/0040-4020(95)00736-R

Reference yield:

Dimethylphenylsilane (766-77-8) → (-)-(4R,5S)-5-((1'S)-hydroxypropyl)-4-(phenyldimethylsilyl)-dihydrofuran-2-one (142730-72-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / bis(2,5-norbornene)tris(tert-butyl)phosphine-platinum⁽⁰⁾ / tetrahydrofuran / 18 h / Heating

2: 1.) titanium tetraisopropoxide, L-(+)-diethyl tartrate, 4 A molecular sieves, 2.) 5.48 M tert-butylhydroperoxide, 3.) dimethyl sulphide / 1.) CH₂Cl₂, 20 min, 2.) CH₂Cl₂, -20 deg C, 48 h, 3.) CH₂Cl₂, 1 h

3: 93 percent / propionic acid / toluene / 30 min, reflux, addition repeated 3 times

4: 2 percent w/v OsO₄, K₃Fe(CN)6, K₂CO₃, dihyroquinidine 4-chlorobenzoate / 2-methyl-propan-2-ol; H₂O / 18 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; osmium(VIII) oxide; dimethylsulfide; diethyl (2R,3R)-tartrate; dihydroquinidine 9-O-(4-chlorobenzoate); 4 A molecular sieve; potassium carbonate; propionic acid; potassium hexacyanoferrate(III); bis(2,5-norbornene)tris(tert-butyl)phosphine-platinum⁽⁰⁾; In tetrahydrofuran; water; toluene; tert-butyl alcohol;

DOI:10.1016/0040-4020(95)00736-R

upstream raw materials:

(+)-methyl (R)-E-3-(phenyldimethylsilyl)hept-4-enoate

pent-1-yn-3-ol

Dimethylphenylsilane

(+/-)-E-1-(phenyldimethylsilyl)pent-1-en-3-ol