(3R,6S)-6-((S)-3-Benzyloxy-2-methoxy-propyl)-3-methyl-tetrahydro-pyran-2-one

Base Information

• Chemical Name: (3R,6S)-6-((S)-3-Benzyloxy-2-methoxy-propyl)-3-methyl-tetrahydro-pyran-2-one
• CAS No.: 156516-22-2
• Molecular Formula: C₁₇H₂₄O₄
• Molecular Weight: 292.375
• Mol file: 156516-22-2.mol

Synonyms:(3R,6S)-6-((S)-3-Benzyloxy-2-methoxy-propyl)-3-methyl-tetrahydro-pyran-2-one

Chemical Property of (3R,6S)-6-((S)-3-Benzyloxy-2-methoxy-propyl)-3-methyl-tetrahydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,6S)-6-((S)-3-Benzyloxy-2-methoxy-propyl)-3-methyl-tetrahydro-pyran-2-one

There total 22 articles about (3R,6S)-6-((S)-3-Benzyloxy-2-methoxy-propyl)-3-methyl-tetrahydro-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: 90.0%

(2R,5S,7S)-8-Benzyloxy-7-methoxy-2-methyl-octane-1,5-diol → (3R,6S)-6-((S)-3-Benzyloxy-2-methoxy-propyl)-3-methyl-tetrahydro-pyran-2-one (156516-22-2)

Guidance literature:

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 1.16667h; Inert atmosphere; Molecular sieve;

DOI:10.1002/chem.200801656

Reference yield:

(-)-(2S,3R)-2,3-epoxy-4-(benzyloxy)-1-butanol (78513-07-2) → (3R,6S)-6-((S)-3-Benzyloxy-2-methoxy-propyl)-3-methyl-tetrahydro-pyran-2-one (156516-22-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 80 percent / pyridine-sulfur trioxide activated DMSO, Et₃N / CH₂Cl₂ / 0 deg C --> room temp.

2: 68 percent / LiCl, DBU / acetonitrile / Ambient temperature

3: DIBAL-H / CH₂Cl₂ / -78 °C

4: pyridine / CH₂Cl₂ / 0 °C

5: 94 percent / NaH / 0 °C

6: 88 percent / DIBAL-H / CH₂Cl₂ / -78 °C

7: 80 percent / 10percent Ti(O-iPr)4, 14percent (-)-diethyl tartarate, t-BuOOH, 4 Angstroem powdered molecular sieves / CH₂Cl₂ / -23 °C

8: 60 percent / tetra-n-propylammonium perruthenate, N-methylmorpholine N-oxide, 4 Angstroem mol. sieves / CH₂Cl₂; acetonitrile

9: 83 percent / KHMDS / tetrahydrofuran / 0 deg C --> room temp.

10: 1.) Fe₂(CO)9 / 1.) THF; 2.) benzene, 280 atm, 70 deg C, 2 d

11: H₂ / PtO₂ / ethyl acetate / 760 Torr / Ambient temperature

12: LDA / tetrahydrofuran / -78 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrapropylammonium perruthennate; diiron nonacarbonyl; 4 A molecular sieve; hydrogen; sulfur trioxide pyridine complex; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; (-)-diethyl tartrate; triethylamine; lithium chloride; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4039(00)73059-0

Reference yield:

(Z)-4-benzyloxy-but-2-en-1-ol (81028-03-7) → (3R,6S)-6-((S)-3-Benzyloxy-2-methoxy-propyl)-3-methyl-tetrahydro-pyran-2-one (156516-22-2)

Guidance literature:

Multi-step reaction with 13 steps

1: Ti(Oi-Pr)4, (+)-diethyl tartrate, t-BuOOH / CH₂Cl₂ / -25 °C

2: 80 percent / pyridine-sulfur trioxide activated DMSO, Et₃N / CH₂Cl₂ / 0 deg C --> room temp.

3: 68 percent / LiCl, DBU / acetonitrile / Ambient temperature

4: DIBAL-H / CH₂Cl₂ / -78 °C

5: pyridine / CH₂Cl₂ / 0 °C

6: 94 percent / NaH / 0 °C

7: 88 percent / DIBAL-H / CH₂Cl₂ / -78 °C

8: 80 percent / 10percent Ti(O-iPr)4, 14percent (-)-diethyl tartarate, t-BuOOH, 4 Angstroem powdered molecular sieves / CH₂Cl₂ / -23 °C

9: 60 percent / tetra-n-propylammonium perruthenate, N-methylmorpholine N-oxide, 4 Angstroem mol. sieves / CH₂Cl₂; acetonitrile

10: 83 percent / KHMDS / tetrahydrofuran / 0 deg C --> room temp.

11: 1.) Fe₂(CO)9 / 1.) THF; 2.) benzene, 280 atm, 70 deg C, 2 d

12: H₂ / PtO₂ / ethyl acetate / 760 Torr / Ambient temperature

13: LDA / tetrahydrofuran / -78 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrapropylammonium perruthennate; diiron nonacarbonyl; 4 A molecular sieve; hydrogen; sulfur trioxide pyridine complex; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-Weinsaeure-diethylester; (-)-diethyl tartrate; triethylamine; lithium chloride; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4039(00)73059-0

upstream raw materials:

methyl iodide

(-)-(2S,3R)-2,3-epoxy-4-(benzyloxy)-1-butanol

(Z)-4-benzyloxy-but-2-en-1-ol

(2S)-1-(benzyloxy)pent-4-en-2-ol

Downstream raw materials:

C₂₃H₄₀O₄Si

sirolimus

C₆₉H₁₂₁O₁₃Si₃N