(2S,3S,4R,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4R,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 851760-14-0
• Molecular Formula: C₂₆H₄₄O₈Si
• Molecular Weight: 512.716
• Mol file: 851760-14-0.mol

Synonyms:(2S,3S,4R,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,3S,4R,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 16 articles about (2S,3S,4R,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl 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: 88.0%

(2S,3R,4R,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (851759-70-1) + t-butyldimethylsiyl triflate (69739-34-0) → (2S,3S,4R,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (851760-14-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 - 0 ℃; for 2h;

DOI:10.1021/ol0501875

Reference yield:

2,3,5,6-tetramethoxy-4-methyl-benzaldehyde (851759-66-5) → (2S,3S,4R,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (851760-14-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 86.8 percent / TMSOTf / CH₂Cl₂ / -50 °C

2: 10 percent / aq. EDTA; 1,1,1-trifluoroacetone; Oxone(R) / NaHCO₃ / acetonitrile / 2 h / -20 °C

3: 69 percent / K₂CO₃ / methanol / 20 °C

4: 91 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: 90 percent / CeCl₃*7H₂O; NaBH₄ / methanol / -78 - 20 °C

6: 99 percent / H₂ / Pd/C / methanol / 4 h / 20 °C

7: 88 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 - 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride; oxone; oxalyl dichloride; ethylenediaminetetraacetic acid; 1,1,1-trifluoro-2-propanone; trimethylsilyl trifluoromethanesulfonate; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; sodium hydrogencarbonate; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/ol0501875

Reference yield:

(E)-(S)-4-(dimethyl-phenyl-silanyl)-pent-3-en-2-ol (851759-97-2) → (2S,3S,4R,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (851760-14-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: DCC; DMAP / toluene / 0 - 20 °C

2.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: TMSCl / tetrahydrofuran / -78 - 20 °C

3.1: NaHCO₃; adogen-464 / CH₂Cl₂ / 20 °C

4.1: DDQ / CH₂Cl₂; H₂O / 0 - 20 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

6.1: 86.8 percent / TMSOTf / CH₂Cl₂ / -50 °C

7.1: 10 percent / aq. EDTA; 1,1,1-trifluoroacetone; Oxone(R) / NaHCO₃ / acetonitrile / 2 h / -20 °C

8.1: 69 percent / K₂CO₃ / methanol / 20 °C

9.1: 91 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

10.1: 90 percent / CeCl₃*7H₂O; NaBH₄ / methanol / -78 - 20 °C

11.1: 99 percent / H₂ / Pd/C / methanol / 4 h / 20 °C

12.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 - 0 °C

With 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; cerium(III) chloride; oxone; oxalyl dichloride; ethylenediaminetetraacetic acid; 1,1,1-trifluoro-2-propanone; trimethylsilyl trifluoromethanesulfonate; Adogen-464; hydrogen; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; palladium on activated charcoal; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/ol0501875

upstream raw materials:

(2S,3R,4R,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

t-butyldimethylsiyl triflate

(E)-(S)-4-(dimethyl-phenyl-silanyl)-pent-3-en-2-ol

2,3,5,6-tetramethoxy-4-methyl-benzaldehyde