(S)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-1-triethylsilanyloxy-propan-2-one

Base Information

• Chemical Name: (S)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-1-triethylsilanyloxy-propan-2-one
• CAS No.: 214476-22-9
• Molecular Formula: C₃₇H₅₀O₆Si
• Molecular Weight: 618.886

Synonyms:(S)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-1-triethylsilanyloxy-propan-2-one

Chemical Property of (S)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-1-triethylsilanyloxy-propan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-1-triethylsilanyloxy-propan-2-one

There total 12 articles about (S)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-1-triethylsilanyloxy-propan-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: 89.0%

triethylsilyl trifluoromethyl sulfonate (79271-56-0) + (S)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-1-hydroxy-propan-2-one (214476-21-8) → (S)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-1-triethylsilanyloxy-propan-2-one (214476-22-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20 ℃; for 0.5h;

DOI:10.1055/s-1998-3140

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → (S)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-1-triethylsilanyloxy-propan-2-one (214476-22-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 91 percent / NaOH, H₂O, Et₃NBnCl / benzene / 5 h / Ambient temperature

2: 78 percent / Bu₃SnH, AIBN / benzene / Heating

3: NIS / 48 h / Ambient temperature

4: Bu₃SnH, AIBN

5: 95 percent / TMSOTf / CH₂Cl₂ / 0 - 20 °C

6: 94 percent / m-CPBA / CH₂Cl₂ / 4 h / 0 - 20 °C

7: 80 percent / ZnCl₂ / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

8: O₃, PPh₃ / CH₂Cl₂ / 0.17 h / -78 °C

9: SiO₂ / CH₂Cl₂ / Ambient temperature

10: tetrahydrofuran; toluene / 6 h / -78 - 20 °C

11: 90 percent / HgO, H₂SO₄, H₂O / acetone / 1 h / Ambient temperature

12: 89 percent / i-Pr₂NEt / CH₂Cl₂ / 0.5 h / -78 - 20 °C

With sodium hydroxide; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; sulfuric acid; N-benzyl-N,N,N-triethylammonium chloride; water; tri-n-butyl-tin hydride; silica gel; ozone; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; mercury(II) oxide; zinc(II) chloride; In tetrahydrofuran; dichloromethane; acetone; toluene; benzene;

DOI:10.1055/s-1998-3140

Reference yield:

3,4,6-tri-O-benzyl-1,5-anhydro-2-deoxy-1,2-C-methylene-D-glycero-D-gulohexitol (162428-31-1) → (S)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-1-triethylsilanyloxy-propan-2-one (214476-22-9)

Guidance literature:

Multi-step reaction with 10 steps

1: NIS / 48 h / Ambient temperature

2: Bu₃SnH, AIBN

3: 95 percent / TMSOTf / CH₂Cl₂ / 0 - 20 °C

4: 94 percent / m-CPBA / CH₂Cl₂ / 4 h / 0 - 20 °C

5: 80 percent / ZnCl₂ / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

6: O₃, PPh₃ / CH₂Cl₂ / 0.17 h / -78 °C

7: SiO₂ / CH₂Cl₂ / Ambient temperature

8: tetrahydrofuran; toluene / 6 h / -78 - 20 °C

9: 90 percent / HgO, H₂SO₄, H₂O / acetone / 1 h / Ambient temperature

10: 89 percent / i-Pr₂NEt / CH₂Cl₂ / 0.5 h / -78 - 20 °C

With N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; sulfuric acid; water; tri-n-butyl-tin hydride; silica gel; ozone; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; mercury(II) oxide; zinc(II) chloride; In tetrahydrofuran; dichloromethane; acetone; toluene;

DOI:10.1055/s-1998-3140

upstream raw materials:

triethylsilyl trifluoromethyl sulfonate

(S)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-1-hydroxy-propan-2-one

3,4,6-tri-O-benzyl-D-glucal

3,4,6-tri-O-benzyl-1,5-anhydro-2-deoxy-1,2-C-methylene-D-glycero-D-gulohexitol

Downstream raw materials:

(1S,4S,5R,6R)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl)-4-hydroxy-5-methyl-10-(tetrahydro-pyran-2-yloxy)-1,6-bis-triethylsilanyloxy-decan-2-one

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