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

Base Information

• Chemical Name: (R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one
• CAS No.: 194355-07-2
• Molecular Formula: C₂₀H₂₀O₄
• Molecular Weight: 324.376
• Mol file: 194355-07-2.mol

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

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

There total 16 articles about (R)-6-((1R,2R)-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: 100.0%

(R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5,6-dihydro-pyran-2-one (194355-06-1) → (R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one (194355-07-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water;

DOI:10.1021/jo970725u

Reference yield: 50.0%

(6R)-6-[(1S,2R)-1-(benzyloxy)-2-{[tert-butyl(diphenyl)silyl]oxy}-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one (859520-63-1) → (R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one (194355-07-2)

Guidance literature:

With pyridine; hydrogen fluoride; at 20 ℃; for 48h;

DOI:10.1055/s-2005-868518

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,2R)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one (194355-07-2)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1021/jo970725u

upstream raw materials:

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

(6R)-6-[(1S,2R)-1-(benzyloxy)-2-{[tert-butyl(diphenyl)silyl]oxy}-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one

(tert-butyl-diphenyl-silanyloxy)-phenyl-acetic acid methyl ester

(6R)-6-[(1S,2R)-1-(benzyloxy)-2-{[tert-butyl(diphenyl)silyl]oxy}-2-phenylethyl]-3,6-dihydro-2H-pyran-2-one

Downstream raw materials:

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

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

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

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