(5R,8S,10S,13R)-19,21-Dimethoxy-8,10-dimethyl-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17⁽²¹⁾,18-triene

Base Information

• Chemical Name: (5R,8S,10S,13R)-19,21-Dimethoxy-8,10-dimethyl-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17⁽²¹⁾,18-triene
• CAS No.: 199991-92-9
• Molecular Formula: C₃₂H₄₀O₇
• Molecular Weight: 536.665

Synonyms:(5R,8S,10S,13R)-19,21-Dimethoxy-8,10-dimethyl-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17⁽²¹⁾,18-triene

Chemical Property of (5R,8S,10S,13R)-19,21-Dimethoxy-8,10-dimethyl-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17⁽²¹⁾,18-triene

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Technology Process of (5R,8S,10S,13R)-19,21-Dimethoxy-8,10-dimethyl-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17⁽²¹⁾,18-triene

There total 8 articles about (5R,8S,10S,13R)-19,21-Dimethoxy-8,10-dimethyl-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17⁽²¹⁾,18-triene 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: 43.0%

(2S,2'S)-oxybis(propane-2,1-diyl)bis(4-methylbenzenesulfonate) (171753-73-4) + (R)-2-[3-((R)-2-Hydroxy-2-phenyl-ethoxymethyl)-2,5-dimethoxy-benzyloxy]-1-phenyl-ethanol (188303-46-0) → (5R,8S,10S,13R)-19,21-Dimethoxy-8,10-dimethyl-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17(21),18-triene (199991-92-9)

Guidance literature:

With sodium hydride; potassium tetrafluoroborate; In N,N-dimethyl-formamide;

DOI:10.1039/a703452k

Reference yield:

2-((S)-2-Benzyloxy-1-methyl-ethoxy)-propan-1-ol (199991-74-7) → (5R,8S,10S,13R)-19,21-Dimethoxy-8,10-dimethyl-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17(21),18-triene (199991-92-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / p-TsOH*H₂O, H₂ / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature

2: 20 percent / pyridine / 3.5 h / 0 - 5 °C

3: 43 percent / NaH, KBF₄ / dimethylformamide

With pyridine; hydrogen; sodium hydride; toluene-4-sulfonic acid; potassium tetrafluoroborate; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1039/a703452k

Reference yield:

2-((S)-2-Benzyloxy-1-methyl-ethoxy)-propionic acid ethyl ester → (5R,8S,10S,13R)-19,21-Dimethoxy-8,10-dimethyl-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17(21),18-triene (199991-92-9)

Guidance literature:

Multi-step reaction with 4 steps

1: LiAlH₄ / tetrahydrofuran / 24 h / Ambient temperature

2: 97 percent / p-TsOH*H₂O, H₂ / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature

3: 20 percent / pyridine / 3.5 h / 0 - 5 °C

4: 43 percent / NaH, KBF₄ / dimethylformamide

With pyridine; lithium aluminium tetrahydride; hydrogen; sodium hydride; toluene-4-sulfonic acid; potassium tetrafluoroborate; palladium on activated charcoal; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1039/a703452k

upstream raw materials:

(2S,2'S)-oxybis(propane-2,1-diyl)bis(4-methylbenzenesulfonate)

(R)-2-[3-((R)-2-Hydroxy-2-phenyl-ethoxymethyl)-2,5-dimethoxy-benzyloxy]-1-phenyl-ethanol

2,4-dimethyl-3-oxapentane-1,5-diol

1,3-bis-bromomethyl-2,5-dimethoxy-benzene

Downstream raw materials:

(5R,8S,10S,13R)-8,10-Dimethyl-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17-diene-19,21-dione

(5R,8S,10S,13R)-19-Methoxy-8,10-dimethyl-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1⁽²⁰⁾,17⁽²¹⁾,18-trien-21-ol

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