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

Base Information

• Chemical Name: (3S,4R,5R)-4-allyl-5-(3-hydroxypropyl)-3-phenylthio-dihydrofuran-2-one
• CAS No.: 920502-64-3
• Molecular Formula: C₁₆H₂₀O₃S
• Molecular Weight: 292.399
• Mol file: 920502-64-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (3S,4R,5R)-4-allyl-5-(3-hydroxypropyl)-3-phenylthio-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: 92.0%

(3S,4R,5R)-4-allyl-3-phenylthio-5-(3-tert-butyldiphenylsilyloxy)propyl-dihydrofuran-2-one (920502-61-0) → (3S,4R,5R)-4-allyl-5-(3-hydroxypropyl)-3-phenylthio-dihydrofuran-2-one (920502-64-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.jorganchem.2006.08.021

Reference yield:

(3S,4R,5R)-5-(2-hydroxy-ethyl)-3-phenylthio-5-(3-tert-butyldiphenylsilyloxy)propyl-dihydrofuran-2-one (920502-60-9) → (3S,4R,5R)-4-allyl-5-(3-hydroxypropyl)-3-phenylthio-dihydrofuran-2-one (920502-64-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: SO₃*pyridine / CH₂Cl₂

1.2: 78 percent / KHMDS / tetrahydrofuran

2.1: 92 percent / tetra-butylammonium fluoride / tetrahydrofuran / 20 °C

With pyridine-SO₃ complex; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.jorganchem.2006.08.021

Reference yield:

(2S,3R)-1,2-dihydro-6-tert-butyldiphenylsilyloxy-hexan-3-yl 2-(phenylthio)acetate (920502-52-9) → (3S,4R,5R)-4-allyl-5-(3-hydroxypropyl)-3-phenylthio-dihydrofuran-2-one (920502-64-3)

Guidance literature:

Multi-step reaction with 6 steps

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

1.2: 74 percent / sodium hydride / benzene / 0.5 h

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

3.1: 90 percent / NaOH / tetrahydrofuran; H₂O

4.1: 86 percent / BH₃*SMe₂ / tetrahydrofuran

5.1: SO₃*pyridine / CH₂Cl₂

5.2: 78 percent / KHMDS / tetrahydrofuran

6.1: 92 percent / tetra-butylammonium fluoride / tetrahydrofuran / 20 °C

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

DOI:10.1016/j.jorganchem.2006.08.021

upstream raw materials:

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

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

(2S,3R)-1,2-dihydro-6-tert-butyldiphenylsilyloxy-hexan-3-yl 2-(phenylthio)acetate

methyl (4R)-4-[(phenylthio)-acetoxy]-7-tert-butyldiphenylsilyloxy-hepten-2(E)-oate

Downstream raw materials:

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