(3S,4R,5R)-4-allyl-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one

Base Information

• Chemical Name: (3S,4R,5R)-4-allyl-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one
• CAS No.: 920502-58-5
• Molecular Formula: C₃₁H₃₆O₃SSi
• Molecular Weight: 516.777
• Mol file: 920502-58-5.mol

Synonyms:(3S,4R,5R)-4-allyl-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one

Chemical Property of (3S,4R,5R)-4-allyl-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5R)-4-allyl-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one

There total 7 articles about (3S,4R,5R)-4-allyl-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-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: 80.0%

(3S,4R,5R)-4-(2-hydroxy-ethyl)-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one (920502-57-4) + Methyltriphenylphosphonium bromide (1779-49-3) → (3S,4R,5R)-4-allyl-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one (920502-58-5)

Guidance literature:

(3S,4R,5R)-4-(2-hydroxy-ethyl)-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one; With pyridine-SO₃ complex; In dichloromethane;

Methyltriphenylphosphonium bromide; With potassium hexamethylsilazane; In tetrahydrofuran;

DOI:10.1016/j.jorganchem.2006.08.021

Reference yield:

(2S,3R)-1,2-dihydro-5-tertbutyldiphenylsilyloxy-pentan-3-yl 2-(phenylthio)acetate (920502-51-8) → (3S,4R,5R)-4-allyl-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one (920502-58-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaIO₄; tetrabutylammonium periodate / methanol; H₂O / 1 h / 20 °C

1.2: 76 percent / sodium hydride / benzene / 0.5 h

2.1: 95 percent / sodium hydride / dimethylformamide / 4 h

3.1: 92 percent / NaOH / tetrahydrofuran; H₂O

4.1: 86 percent / BH₃*SMe₂ / tetrahydrofuran

5.1: SO₃*pyridine / CH₂Cl₂

5.2: 80 percent / KHMDS / tetrahydrofuran

With sodium hydroxide; sodium periodate; pyridine-SO₃ complex; dimethylsulfide borane complex; sodium hydride; tetrabutylammonium periodite; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.jorganchem.2006.08.021

Reference yield:

(2R,3R,4S)-[5-oxo-4-(phenylthio)-2-(2-tert-butyldiphenylsilyloxy)ethyl-tetrahydrofuran-3-yl]acetic acid (920502-56-3) → (3S,4R,5R)-4-allyl-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one (920502-58-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 86 percent / BH₃*SMe₂ / tetrahydrofuran

2.1: SO₃*pyridine / CH₂Cl₂

2.2: 80 percent / KHMDS / tetrahydrofuran

With pyridine-SO₃ complex; dimethylsulfide borane complex; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.jorganchem.2006.08.021

upstream raw materials:

(3S,4R,5R)-4-(2-hydroxy-ethyl)-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one

Methyltriphenylphosphonium bromide

(2S,3R)-1,2-dihydro-5-tertbutyldiphenylsilyloxy-pentan-3-yl 2-(phenylthio)acetate

(2R,3R,4S)-[5-oxo-4-(phenylthio)-2-(2-tert-butyldiphenylsilyloxy)ethyl-tetrahydrofuran-3-yl]acetic acid

Downstream raw materials:

(3S,4R,5R)-4,5-diallyl-3-phenylthio-dihydrofuran-2-one

(3S,4R,5R)-4-allyl-5-(2-hydroxyethyl)-3-phenylthio-dihydrofuran-2-one