(R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3,6-dihydro-pyran-2-one

Base Information

• Chemical Name: (R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3,6-dihydro-pyran-2-one
• CAS No.: 163630-05-5
• Molecular Formula: C₁₆H₁₈O₄
• Molecular Weight: 274.317
• Mol file: 163630-05-5.mol

Synonyms:(R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3,6-dihydro-pyran-2-one

Chemical Property of (R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3,6-dihydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3,6-dihydro-pyran-2-one

There total 5 articles about (R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3,6-dihydro-pyran-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: 87.0%

Acetic acid (2R,3S)-2-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-6-oxo-3,6-dihydro-2H-pyran-3-yl ester (163630-04-4) → (R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3,6-dihydro-pyran-2-one (163630-05-5)

Guidance literature:

With hydrogenchloride; mercury; zinc; In diethyl ether; for 4h; Ambient temperature;

DOI:10.1039/c39950000743

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3,6-dihydro-pyran-2-one (163630-05-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 86 percent / TBHP, Ti(OiPr)4, L-(+)-diisopropyl tartrate, molecular sieves 4 Angstroem / CH₂Cl₂ / -20 °C

2: 90 percent / CHCl₃ / -20 - 0 °C

3: imidazole / tetrahydrofuran / Ambient temperature

4: 15percent aq. NaOH / tetrahydrofuran / Ambient temperature

5: p-TsOH / CH₂Cl₂ / Ambient temperature

6: nBu₄NF / tetrahydrofuran / 0 °C

7: Me₂SO, (COCl)2, Et₃N / CH₂Cl₂ / -78 - -20 °C

8: tetrahydrofuran / -78 - -30 °C

9: 84 percent / TBHP, VO(acac)2 / CH₂Cl₂ / 0 °C

10: 1) CrO₃, 2) NaBH(OAc)3 / 1) HOAc, 25 deg C to 30 deg C, 15 min, 2) iPrOH, HOAc, -10 deg C to r.t.

11: 98 percent / pyridine, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

12: 87 percent / Zn-Hg, HCl / diethyl ether / 4 h / Ambient temperature

With pyridine; 1H-imidazole; chromium(VI) oxide; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium hydroxide; oxalyl dichloride; bis(acetylacetonate)oxovanadium; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; mercury; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform;

DOI:10.1039/c39950000743

Reference yield:

Acetic acid (2S,3R)-2,3-dihydroxy-3-phenyl-propyl ester (163748-92-3) → (R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3,6-dihydro-pyran-2-one (163630-05-5)

Guidance literature:

Multi-step reaction with 8 steps

1: p-TsOH / CH₂Cl₂ / 8 h / Ambient temperature

2: 15percent NaOH / tetrahydrofuran; H₂O / Ambient temperature

3: Me₂SO, (COCl)2, Et₃N / CH₂Cl₂ / -78 - -20 °C

4: tetrahydrofuran / -78 - -30 °C

5: 84 percent / TBHP, VO(acac)2 / CH₂Cl₂ / 0 °C

6: 1) CrO₃, 2) NaBH(OAc)3 / 1) HOAc, 25 deg C to 30 deg C, 15 min, 2) iPrOH, HOAc, -10 deg C to r.t.

7: 98 percent / pyridine, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

8: 87 percent / Zn-Hg, HCl / diethyl ether / 4 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium hydroxide; oxalyl dichloride; bis(acetylacetonate)oxovanadium; sodium tris(acetoxy)borohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; mercury; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1039/c39950000743

upstream raw materials:

Acetic acid (2R,3S)-2-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-6-oxo-3,6-dihydro-2H-pyran-3-yl ester

Acetic acid (2S,3R)-2,3-dihydroxy-3-phenyl-propyl ester

(2S,3R)-2,3-dihydroxy-3-phenylpropanyl tert-butyldiphenylsilyl ether

(2S,3R)-2,3-isopropylidenyloxy-3-phenylpropanyl tert-butyldiphenylsilyl ether

Downstream raw materials:

7,8-di-O-acetyl-goniodiol

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

(6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-5,6-dihydropyran-2-one