(R)-6-((1R,2S)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one

Base Information

• Chemical Name: (R)-6-((1R,2S)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one
• CAS No.: 194355-09-4
• Molecular Formula: C₂₀H₂₀O₄
• Molecular Weight: 324.376
• Mol file: 194355-09-4.mol

Synonyms:(R)-6-((1R,2S)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one

Chemical Property of (R)-6-((1R,2S)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-((1R,2S)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one

There total 10 articles about (R)-6-((1R,2S)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-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: 59.0%

4-Nitro-benzoic acid (1S,2S)-2-benzyloxy-2-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-phenyl-ethyl ester (194355-08-3) → (-)-(1R,5R,7S,8R)-8-benzyloxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one (194355-10-7) + (R)-6-((1R,2S)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one (194355-09-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; for 1h; Ambient temperature;

DOI:10.1021/jo970725u

Reference yield:

(+)-goniodiol (146236-73-9,96422-52-5) → (R)-6-((1R,2S)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one (194355-09-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / PPh₃, DEAD / benzene / Ambient temperature

2: 31 percent / LiOH / tetrahydrofuran; H₂O / 1 h / Ambient temperature

With lithium hydroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; water; benzene;

DOI:10.1021/jo970725u

Reference yield:

(R)-5-[(1R,2S,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-phenyl-propyl]-5H-furan-2-one (153000-32-9) → (R)-6-((1R,2S)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one (194355-09-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 97 percent / CH₂Cl₂ / 10 h / Ambient temperature

2: DIBALH / diethyl ether / 0.17 h / -78 °C

4: 100 percent / DMAP / CH₂Cl₂ / 0.17 h / Ambient temperature

5: 88 percent / Zn/Hg, HCl / diethyl ether / 0.5 h / -20 °C

6: 90 percent / DBU / tetrahydrofuran / 26 h / Ambient temperature

7: 100 percent / LiOH / tetrahydrofuran; H₂O

8: 97 percent / TiCl₄ / CH₂Cl₂

9: 49 percent / PPh₃, DEAD / benzene / Ambient temperature

10: 31 percent / LiOH / tetrahydrofuran; H₂O / 1 h / Ambient temperature

With hydrogenchloride; dmap; lithium hydroxide; titanium tetrachloride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; mercury; zinc; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; water; benzene;

DOI:10.1021/jo970725u

upstream raw materials:

4-Nitro-benzoic acid (1S,2S)-2-benzyloxy-2-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-phenyl-ethyl ester

(+)-goniodiol

(R)-5-[(1R,2S,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-phenyl-propyl]-5H-furan-2-one

(5R,6R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-hydroxy-5,6-dihydro-pyran-2-one

Downstream raw materials:

(1R,5R,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxa-bicyclo-[3.3.1]-nonan-3-one

(-)-(1R,5R,7S,8R)-8-benzyloxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one