(2R,3S,4S)-4-(tert-butyldimethylsiloxy)-6-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-(oxo)methyl] tetrahydro-6-phenylsulfone-3-methyl-2-(4-benzyloxybutyl)-2H-pyran

Base Information

• Chemical Name: (2R,3S,4S)-4-(tert-butyldimethylsiloxy)-6-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-(oxo)methyl] tetrahydro-6-phenylsulfone-3-methyl-2-(4-benzyloxybutyl)-2H-pyran
• CAS No.: 203515-73-5
• Molecular Formula: C₄₂H₆₆O₈SSi₂
• Molecular Weight: 787.218

Synonyms:

Chemical Property of (2R,3S,4S)-4-(tert-butyldimethylsiloxy)-6-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-(oxo)methyl] tetrahydro-6-phenylsulfone-3-methyl-2-(4-benzyloxybutyl)-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-4-(tert-butyldimethylsiloxy)-6-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-(oxo)methyl] tetrahydro-6-phenylsulfone-3-methyl-2-(4-benzyloxybutyl)-2H-pyran

There total 21 articles about (2R,3S,4S)-4-(tert-butyldimethylsiloxy)-6-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-(oxo)methyl] tetrahydro-6-phenylsulfone-3-methyl-2-(4-benzyloxybutyl)-2H-pyran 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:

(4S,2R,3R)-4-triethylsiloxy-3-methyl(3,4-dihydro-2H-pyran-2-yl) benzotriazolyl ketone (203515-66-6) + (4S,5R,6R)-6-(4-benzyloxybutyl)-5-methyl-4-(tert-butyldimethylsiloxy)-2-phenylsulfone-tetrahydro-2H-pyran (203515-59-7) → (2R,3S,4S)-4-(tert-butyldimethylsiloxy)-6-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-(oxo)methyl] tetrahydro-6-phenylsulfone-3-methyl-2-(4-benzyloxybutyl)-2H-pyran (203515-73-5)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; Yield given;

DOI:10.1002/anie.199727411

Reference yield:

triethylsilyl chloride (994-30-9) → (2R,3S,4S)-4-(tert-butyldimethylsiloxy)-6-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-(oxo)methyl] tetrahydro-6-phenylsulfone-3-methyl-2-(4-benzyloxybutyl)-2H-pyran (203515-73-5)

Guidance literature:

Multi-step reaction with 9 steps

1: imidazole

2: DIBALH / -78 °C

3: 81 percent / POCl₃, pyridine / 80 °C

4: 99 percent / LDBB / tetrahydrofuran / -78 °C

5: 1.) SO₃*pyridine, DMSO, 2.) Et₃N

6: NaClO₂, 2-methyl-2-butene, ethyl-1-propenyl ether / 2-methyl-propan-2-ol / pH 5.5

7: 1-chloro-N,N-trimethylpropenylamine

8: pyridine, DMAP

9: LDA / tetrahydrofuran / -78 °C

With pyridine; 1H-imidazole; dmap; sodium chlorite; 2-methyl-but-2-ene; lithium 4,4′-di(tert-butyl)biphenyl; pyridine-SO₃ complex; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; ethyl-1-propenyl ether; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; tert-butyl alcohol;

DOI:10.1002/anie.199727411

Reference yield:

phenylthiotrimethylsilane (4551-15-9) → (2R,3S,4S)-4-(tert-butyldimethylsiloxy)-6-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-(oxo)methyl] tetrahydro-6-phenylsulfone-3-methyl-2-(4-benzyloxybutyl)-2H-pyran (203515-73-5)

Guidance literature:

Multi-step reaction with 4 steps

1: ZnI₂

2: NaH, Bu₄NI

3: 97 percent / m-CPBA, NaHCO₃

4: LDA / tetrahydrofuran / -78 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1002/anie.199727411

upstream raw materials:

(4S,2R,3R)-4-triethylsiloxy-3-methyl(3,4-dihydro-2H-pyran-2-yl) benzotriazolyl ketone

(4S,5R,6R)-6-(4-benzyloxybutyl)-5-methyl-4-(tert-butyldimethylsiloxy)-2-phenylsulfone-tetrahydro-2H-pyran

triethylsilyl chloride

phenylthiotrimethylsilane

Downstream raw materials:

(1R,3R,4S,5R,6S)-3-{(S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-triethylsilanyloxy-methyl}-4-methyl-5-triethylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]heptane

C₅₅H₁₀₂O₉Si₄

(2R,3S,4S,6R)-4-(tert-butyldimethylsiloxy)-6-[(S)-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-yl] (triethylsiloxy)methyl] tetrahydro-6-methoxy-3-methyl-2-(4-benzyloxybutyl)-2H-pyran

(2R,3S,4S,6R)-4-(tert-butyldimethylsiloxy)-6-[(S)-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-yl] (hydroxy)methyl] tetrahydro-6-methoxy-3-methyl-2-(4-benzyloxybutyl)-2H-pyran

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