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

Base Information

• Chemical Name: (5S,6R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-hydroxy-5,6-dihydro-pyran-2-one
• CAS No.: 194355-01-6
• Molecular Formula: C₂₆H₃₄O₅Si
• Molecular Weight: 454.638
• Mol file: 194355-01-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (5S,6R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-hydroxy-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: 74.0%

4-Nitro-benzoic acid (2R,3S)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester (194355-00-5) → (5S,6R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-hydroxy-5,6-dihydro-pyran-2-one (194355-01-6)

Guidance literature:

With water; potassium carbonate; In tetrahydrofuran; for 4h; Ambient temperature;

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) → (5S,6R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-hydroxy-5,6-dihydro-pyran-2-one (194355-01-6)

Guidance literature:

Multi-step reaction with 5 steps

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

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

4: 96 percent / PPh₃, DEAD / benzene / 5 h / Ambient temperature

5: 74 percent / K₂CO₃, H₂O / tetrahydrofuran / 4 h / Ambient temperature

With water; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo970725u

Reference yield:

(5R,6R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-hydroxy-5,6-dihydro-pyran-2-one (181534-68-9) → (5S,6R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-hydroxy-5,6-dihydro-pyran-2-one (194355-01-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / PPh₃, DEAD / benzene / 5 h / Ambient temperature

2: 74 percent / K₂CO₃, H₂O / tetrahydrofuran / 4 h / Ambient temperature

With water; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; benzene;

DOI:10.1021/jo970725u

upstream raw materials:

4-Nitro-benzoic acid (2R,3S)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester

(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

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

Downstream raw materials:

Acetic acid (2R,3S)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester

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