4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-4-yl ester
• CAS No.: 220775-00-8
• Molecular Formula: C₄₃H₅₂O₇SSi
• Molecular Weight: 741.033
• Mol file: 220775-00-8.mol

Synonyms:4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-4-yl ester

Chemical Property of 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-4-yl ester

There total 5 articles about 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-4-yl ester 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: 85.0%

levulinic acid (123-76-2) + (2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol (220774-98-1) → 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-4-yl ester (220775-00-8)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 24h; Heating;

DOI:10.1016/S0040-4039(98)80003-8

Reference yield:

(2S,3R,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,5-diol (220774-88-9) → 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-4-yl ester (220775-00-8)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine, DMAP / 1 h / 0 - 10 °C

2: 75 percent / PDC, Ac₂O / CH₂Cl₂ / 2 h / Heating

3: CeCl₃ / toluene / -76 deg C -> r.t., 14 h

4: 90 percent / TBAF / tetrahydrofuran / 0.25 h / Ambient temperature

5: 85 percent / DCC, DMAP / CH₂Cl₂ / 24 h / Heating

With pyridine; dmap; dipyridinium dichromate; cerium(III) chloride; tetrabutyl ammonium fluoride; acetic anhydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0040-4039(98)80003-8

Reference yield:

phenyl 3-O-TBDMS-4-C-methyl-6-O-trityl-1-thio-β-D-glucopyranoside (220774-94-7) → 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-4-yl ester (220775-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / TBAF / tetrahydrofuran / 0.25 h / Ambient temperature

2: 85 percent / DCC, DMAP / CH₂Cl₂ / 24 h / Heating

With dmap; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(98)80003-8

upstream raw materials:

levulinic acid

(2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol

(2S,3R,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,5-diol

phenyl 3-O-TBDMS-4-C-methyl-6-O-trityl-1-thio-β-D-glucopyranoside

Downstream raw materials:

4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-3-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester