(2S,3R,4S)-2-Hydroxymethyl-4-((11S,12S)-11-hydroxy-12-methyl-tetradecyl)-1-(toluene-4-sulfonyl)-azetidin-3-ol

Base Information

• Chemical Name: (2S,3R,4S)-2-Hydroxymethyl-4-((11S,12S)-11-hydroxy-12-methyl-tetradecyl)-1-(toluene-4-sulfonyl)-azetidin-3-ol
• CAS No.: 221217-34-1
• Molecular Formula: C₂₆H₄₅NO₅S
• Molecular Weight: 483.713
• Mol file: 221217-34-1.mol

Synonyms:(2S,3R,4S)-2-Hydroxymethyl-4-((11S,12S)-11-hydroxy-12-methyl-tetradecyl)-1-(toluene-4-sulfonyl)-azetidin-3-ol

Chemical Property of (2S,3R,4S)-2-Hydroxymethyl-4-((11S,12S)-11-hydroxy-12-methyl-tetradecyl)-1-(toluene-4-sulfonyl)-azetidin-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-2-Hydroxymethyl-4-((11S,12S)-11-hydroxy-12-methyl-tetradecyl)-1-(toluene-4-sulfonyl)-azetidin-3-ol

There total 60 articles about (2S,3R,4S)-2-Hydroxymethyl-4-((11S,12S)-11-hydroxy-12-methyl-tetradecyl)-1-(toluene-4-sulfonyl)-azetidin-3-ol 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%

(3S,4S)-14-((2S,3R,4S)-3-(benzyloxy)-4-((benzyloxy)methyl)-1-(p-tosyl)azetidin-2-yl)-3-methyltetradecan-4-ol → (2S,3R,4S)-2-Hydroxymethyl-4-((11S,12S)-11-hydroxy-12-methyl-tetradecyl)-1-(toluene-4-sulfonyl)-azetidin-3-ol (221217-34-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; for 4h;

DOI:10.1016/j.tetlet.2013.10.095

Reference yield:

divinylcarbinol (922-65-6) → (2S,3R,4S)-2-Hydroxymethyl-4-((11S,12S)-11-hydroxy-12-methyl-tetradecyl)-1-(toluene-4-sulfonyl)-azetidin-3-ol (221217-34-1)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) TBHP, D-(-)-DIPT, Ti(O-iso-Pr)4, 4 Angstroem molecular sieves, 2.) 0.5N NaOH / 1.) CH₂Cl₂, -20 deg C, 10 d, 2.) -10 deg C

2: 87 percent / NaH, Bu₄NI / tetrahydrofuran

3: DHQ-PYR, K₂2(OH)4>, K₂CO₃, K₃ / 2-methyl-propan-2-ol; H₂O

4: PTS / CH₂Cl₂

5: 87 percent / NaN₃, NH₄Cl / various solvent(s) / Heating

6: 87 percent / NaH, Bu₄NI / tetrahydrofuran / Heating

7: LiAlH₄ / tetrahydrofuran

8: Et₃N / CH₂Cl₂

9: 95 percent / 2N HCl / methanol / 40 °C

10: DMAP, Et₃N / CH₂Cl₂

11: 60 percent / Ph₃P, DEAD / CH₂Cl₂

12: Bu₄NF / tetrahydrofuran

13: 60 percent / NaDMSO / tetrahydrofuran / -78 - -10 °C

14: 92 percent / NH₂OH, EtOAc / dimethylformamide / 90 - 100 °C

15: 86 percent / LiAlH₄ / diethyl ether

16: 79 percent / H₂ / 10 percent Pd/C / ethanol

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium hydroxide; lithium aluminium tetrahydride; sodium azide; K2; 4 A molecular sieve; dimsylsodium; tetrabutyl ammonium fluoride; hydrogen; hydroxylamine; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; ammonium chloride; ethyl acetate; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/S0040-4039(98)02345-4

Reference yield:

1,10-Decanediol (112-47-0) → (2S,3R,4S)-2-Hydroxymethyl-4-((11S,12S)-11-hydroxy-12-methyl-tetradecyl)-1-(toluene-4-sulfonyl)-azetidin-3-ol (221217-34-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / HBr / benzene / Heating

2: HBr / benzene / Heating

3: 4 Angstroem molecular sieves / toluene / -78 °C

4: 96 percent / pyridine, DMAP / CH₂Cl₂

5: 95 percent / 130 °C

6: 60 percent / NaDMSO / tetrahydrofuran / -78 - -10 °C

7: 92 percent / NH₂OH, EtOAc / dimethylformamide / 90 - 100 °C

8: 86 percent / LiAlH₄ / diethyl ether

9: 79 percent / H₂ / 10 percent Pd/C / ethanol

With pyridine; dmap; lithium aluminium tetrahydride; 4 A molecular sieve; dimsylsodium; hydrogen bromide; hydrogen; hydroxylamine; ethyl acetate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4039(98)02345-4

upstream raw materials:

(2S,3R,4S,11'S,12'S)-3-tert-Butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-4-(11'-tert-butyldimethylsilyloxy-12'-methyltetradecyl)-N-p-tolylsulfonylazetidine

divinylcarbinol

1,10-Decanediol

1-bromo-10-decanol

Downstream raw materials:

(15S,16S)-Penaresidin A

Refernces

• 1、 Liu, Ding-Guo,Lin, Guo-Qiang. "Novel enantioselective synthesis of penaresidin A and Allo-penaresidin A via the construction of a highly functionalized azetidine". . p. 337 - 340. Retrieved 2007/10/03.