(+)-(1R,4S,4aR,9S,10S,14aR,15S,18R,18aS,22aS)-eicosahydro-4,15,23,23,24,24-hexamethyl-9,10-bis-(benzyloxymethyl)-1,4:15,18-dimethanodibenzo<1,4,7,10,13,16>hexaoxacyclooctadecin

Base Information

• Chemical Name: (+)-(1R,4S,4aR,9S,10S,14aR,15S,18R,18aS,22aS)-eicosahydro-4,15,23,23,24,24-hexamethyl-9,10-bis-(benzyloxymethyl)-1,4:15,18-dimethanodibenzo<1,4,7,10,13,16>hexaoxacyclooctadecin
• CAS No.: 104128-80-5
• Molecular Formula: C₄₄H₆₄O₈
• Molecular Weight: 720.987
• Mol file: 104128-80-5.mol

Synonyms:

Chemical Property of (+)-(1R,4S,4aR,9S,10S,14aR,15S,18R,18aS,22aS)-eicosahydro-4,15,23,23,24,24-hexamethyl-9,10-bis-(benzyloxymethyl)-1,4:15,18-dimethanodibenzo<1,4,7,10,13,16>hexaoxacyclooctadecin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1R,4S,4aR,9S,10S,14aR,15S,18R,18aS,22aS)-eicosahydro-4,15,23,23,24,24-hexamethyl-9,10-bis-(benzyloxymethyl)-1,4:15,18-dimethanodibenzo<1,4,7,10,13,16>hexaoxacyclooctadecin

There total 16 articles about (+)-(1R,4S,4aR,9S,10S,14aR,15S,18R,18aS,22aS)-eicosahydro-4,15,23,23,24,24-hexamethyl-9,10-bis-(benzyloxymethyl)-1,4:15,18-dimethanodibenzo<1,4,7,10,13,16>hexaoxacyclooctadecin 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%

(2S,3S)-1,4-bis(benzyloxy)-2,3-butanediol (17401-06-8) + (+)-(1R,2R,3S,4S)-1,2-bis<2-(2'-tosyloxyethoxy)-1,7,7-trimethylbicyclo<2.2.1>hept-3-yloxy>ethane (73440-86-5,73494-45-8) → (+)-(1R,4S,4aR,9S,10S,14aR,15S,18R,18aS,22aS)-eicosahydro-4,15,23,23,24,24-hexamethyl-9,10-bis-(benzyloxymethyl)-1,4:15,18-dimethanodibenzo<1,4,7,10,13,16>hexaoxacyclooctadecin (104128-80-5,104155-01-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 50 ℃; for 20h;

Reference yield: 69.0%

(2S,3S)-1,4-bis(benzyloxy)-2,3-butanediol (17401-06-8) + (1R,2S,3R,4S)-1,2-bis-<2-(2'-tosyloxy)ethoxy-1,7,7-trimethylbicyclo<2.2.1>hept-3-yloxy>-ethane (73440-86-5,73494-45-8) → C44H64O8 (104128-80-5,104155-01-3)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 60 ℃; for 20h;

Reference yield:

2-endo-3-endo camphane-2,3-diol (73522-22-2) → (+)-(1R,4S,4aR,9S,10S,14aR,15S,18R,18aS,22aS)-eicosahydro-4,15,23,23,24,24-hexamethyl-9,10-bis-(benzyloxymethyl)-1,4:15,18-dimethanodibenzo<1,4,7,10,13,16>hexaoxacyclooctadecin (104128-80-5,104155-01-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 35 percent / 55 percent NaH in oil / dimethylformamide / 3 h / Ambient temperature

2: 1.) 55 percent NaH in oil; 2.) cc. HCl / 1.) DMF, r.t., 2 h.; 2.) MeOH, reflux, 2 h.

3: 95 percent / pyridine / 15 h / 0 °C

4: 90 percent / 55 percent NaH in oil / dimethylformamide / 2.5 h / Ambient temperature

5: 97 percent / cc. HCl, H₂ / 5 percent Pd-C / ethanol / 8 h / Ambient temperature

6: 1.) 55 percent NaH in oil; 2.) cc. HCl / 1.) DMF, r.t., 24 h.; 2.) MeOH, r.t., 1.5 h.

7: 80 percent / pyridine / 20 h / Ambient temperature

8: 85 percent / 55 percent NaH in oil / dimethylformamide / 20 h / 50 °C

With pyridine; hydrogenchloride; hydrogen; sodium hydride; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

upstream raw materials:

(2S,3S)-1,4-bis(benzyloxy)-2,3-butanediol

(1R,2S,3R,4S)-1,2-bis-<2-(2'-tosyloxy)ethoxy-1,7,7-trimethylbicyclo<2.2.1>hept-3-yloxy>-ethane

(1R)-(-)-cis-3-hydroxyisoborneol

(-)-(1R,2S,3R,4S)-2-(2-tetrahydropyranyloxy)ethoxy-3-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptane

Downstream raw materials:

C₄₄H₆₀O₈S₂

(-)-(1R,4S,4aS,9S,10S,14aS,15S,18R,18aR,22aR)-eicosahydro-4,15,23,23,24,24-hexamethyl-9,10-bis-(tosyloxymethyl)-1,4:15,18-dimethanodibenzo<1,4,7,10,13,16>hexaoxacyclooctadecin

(+)-(1R,4S,4aR,9R,10R,14aR,15S,18R,18aS,22aS)-eicosahydro-4,15,23,23,24,24-hexamethyl-9,10-bis(benzoylthiomethyl)-1,4:15,18-dimethanodibenzo<1,4,7,10,13,16>hexaoxacyclooctadecin

(+)-(1R,4S,4aR,9S,10S,14aR,15S,18R,18aS,22aS)-eicosahydro-4,15,23,23,24,24-hexamethyl-9,10-bis-(tosyloxymethyl)-1,4:15,18-dimethanodibenzo<1,4,7,10,13,16>hexaoxacyclooctadecin