(5S,6R)-5-hydroxy-6-<(1R,2R)-1,2-isopropylidenyloxy-2-phenylethyl>-5,6-dihydropyran-2-one

Base Information

• Chemical Name: (5S,6R)-5-hydroxy-6-<(1R,2R)-1,2-isopropylidenyloxy-2-phenylethyl>-5,6-dihydropyran-2-one
• CAS No.: 162466-16-2
• Molecular Formula: C₁₆H₁₈O₅
• Molecular Weight: 290.316
• Mol file: 162466-16-2.mol

Synonyms:(5S,6R)-5-hydroxy-6-<(1R,2R)-1,2-isopropylidenyloxy-2-phenylethyl>-5,6-dihydropyran-2-one

Chemical Property of (5S,6R)-5-hydroxy-6-<(1R,2R)-1,2-isopropylidenyloxy-2-phenylethyl>-5,6-dihydropyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6R)-5-hydroxy-6-<(1R,2R)-1,2-isopropylidenyloxy-2-phenylethyl>-5,6-dihydropyran-2-one

There total 11 articles about (5S,6R)-5-hydroxy-6-<(1R,2R)-1,2-isopropylidenyloxy-2-phenylethyl>-5,6-dihydropyran-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:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (5S,6R)-5-hydroxy-6-<(1R,2R)-1,2-isopropylidenyloxy-2-phenylethyl>-5,6-dihydropyran-2-one (162466-16-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 86 percent / 4 Angstroem mol. sieves, (L)+diisopropyl tartarate, Ti(i-PrO)4, t-BuOOH / CH₂Cl₂ / 1 h / -15 - -5 °C

2: 90 percent / CHCl₃ / 3 h / -20 - 0 °C

3: 94 percent / imidazole / tetrahydrofuran / 24 h / Ambient temperature

4: 83 percent / K₂CO₃ / H₂O; methanol / 2 h / Ambient temperature

5: 91 percent / p-TsOH / CH₂Cl₂ / 12 h / Ambient temperature

6: 94 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

7: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 - -20 °C

8: 74 percent / n-BuLi / tetrahydrofuran / 2 h / -78 - -40 °C

9: 86 percent / TBHP, VO(acac) / CH₂Cl₂ / 10 h / 0 °C

10: 1.) CrO₃; 2.) NaBH(OAc)3 / 1.) AcOH, 15 min, 30 deg C; 2.) IPA/AcOH, -10 deg C, 1 h

With 1H-imidazole; chromium(VI) oxide; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; bis(acetylacetonate)oxovanadium; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; chloroform; water;

DOI:10.1016/0040-4020(94)01025-U

Reference yield:

(4R,5R)-cis-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-carbaldehyde (130718-77-3) → (5S,6R)-5-hydroxy-6-<(1R,2R)-1,2-isopropylidenyloxy-2-phenylethyl>-5,6-dihydropyran-2-one (162466-16-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / n-BuLi / tetrahydrofuran / 2 h / -78 - -40 °C

2: 86 percent / TBHP, VO(acac) / CH₂Cl₂ / 10 h / 0 °C

3: 1.) CrO₃; 2.) NaBH(OAc)3 / 1.) AcOH, 15 min, 30 deg C; 2.) IPA/AcOH, -10 deg C, 1 h

With chromium(VI) oxide; tert.-butylhydroperoxide; n-butyllithium; bis(acetylacetonate)oxovanadium; sodium tris(acetoxy)borohydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4020(94)01025-U

Reference yield:

(1S,2R,3R)-1-(2-furyl)-2,3-isopropylidenyloxy-3-phenyl-1-propanol (162600-01-3) → (5S,6R)-5-hydroxy-6-<(1R,2R)-1,2-isopropylidenyloxy-2-phenylethyl>-5,6-dihydropyran-2-one (162466-16-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / TBHP, VO(acac) / CH₂Cl₂ / 10 h / 0 °C

2: 1.) CrO₃; 2.) NaBH(OAc)3 / 1.) AcOH, 15 min, 30 deg C; 2.) IPA/AcOH, -10 deg C, 1 h

With chromium(VI) oxide; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; sodium tris(acetoxy)borohydride; In dichloromethane;

DOI:10.1016/0040-4020(94)01025-U

upstream raw materials:

(4R,5R)-cis-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-carbaldehyde

(2R,3S)-(3-phenyloxiran-2-yl)methanol

((4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)methanol

(2S,3R)-3-acetoxyl-3-phenyl-1,2-propanediol

Downstream raw materials:

(5S,6R)-6-[(1S,2R)-1-(benzyloxy)-1,2-dihydroxy-2-phenylethyl]-5-hydroxy-5,6-dihydro-2H-pyran-2-one

(+)-goniofufurone

(6R,7R,8R)-goniodiol-8-monoacetate

8-O-acetylgoniotriol