(2R,3S,5R,6S)-2-((E)-(1S,3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-methoxy-3,5-dimethyl-non-5-enyl)-3,6-dimethoxy-5-methyl-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3S,5R,6S)-2-((E)-(1S,3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-methoxy-3,5-dimethyl-non-5-enyl)-3,6-dimethoxy-5-methyl-tetrahydro-pyran
• CAS No.: 123444-74-6
• Molecular Formula: C₄₂H₅₈O₇
• Molecular Weight: 674.918
• Mol file: 123444-74-6.mol

Synonyms:(2R,3S,5R,6S)-2-((E)-(1S,3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-methoxy-3,5-dimethyl-non-5-enyl)-3,6-dimethoxy-5-methyl-tetrahydro-pyran

Chemical Property of (2R,3S,5R,6S)-2-((E)-(1S,3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-methoxy-3,5-dimethyl-non-5-enyl)-3,6-dimethoxy-5-methyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,5R,6S)-2-((E)-(1S,3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-methoxy-3,5-dimethyl-non-5-enyl)-3,6-dimethoxy-5-methyl-tetrahydro-pyran

There total 21 articles about (2R,3S,5R,6S)-2-((E)-(1S,3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-methoxy-3,5-dimethyl-non-5-enyl)-3,6-dimethoxy-5-methyl-tetrahydro-pyran 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: 76.0%

(2R,3S,5R,6S)-2-((E)-(1S,3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-hydroxy-3,5-dimethyl-non-5-enyl)-6-methoxy-5-methyl-tetrahydro-pyran-3-ol + methyl iodide (74-88-4) → (2R,3S,5R,6S)-2-((E)-(1S,3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-methoxy-3,5-dimethyl-non-5-enyl)-3,6-dimethoxy-5-methyl-tetrahydro-pyran (123444-74-6)

Guidance literature:

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

DOI:10.1016/S0040-4039(01)80352-X

Reference yield:

methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methylene-α-D-erythro-hexopyranoside (35905-41-0) → (2R,3S,5R,6S)-2-((E)-(1S,3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-methoxy-3,5-dimethyl-non-5-enyl)-3,6-dimethoxy-5-methyl-tetrahydro-pyran (123444-74-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 67 percent / hydrogen / Pd-C / ethanol

2: 92 percent / hydrogen / Pd(OH)2 / ethanol

3: 84 percent / Ph₃P, DIAD / tetrahydrofuran

4: 89 percent / imidazole / DMAP / dimethylformamide / 70 °C

5: 96 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6: RuCl₃, NaIO₄ / CCl₄; acetonitrile; H₂O

7: K₂CO₃ / dimethylformamide

8: 1.) n-butyllithium / 1.) THF, -78 deg C, 10 min, 2.) 0 deg C, 1 h

9: 84 percent / tri-n-butyltin hydride, AIBN / toluene / Heating

10: 92 percent / HF-pyridine / tetrahydrofuran

11: acetic acid; acetonitrile / 18 h / -40 °C

12: 76 percent / NaH / dimethylformamide

With 1H-imidazole; ruthenium trichloride; sodium periodate; n-butyllithium; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; hydrogen; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; pyridine hydrogenfluoride; triphenylphosphine; dmap; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4039(01)80352-X

Reference yield:

(2R,3S,5R,6S)-2-Hydroxymethyl-6-methoxy-5-methyl-tetrahydro-pyran-3-ol (123474-66-8) → (2R,3S,5R,6S)-2-((E)-(1S,3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-methoxy-3,5-dimethyl-non-5-enyl)-3,6-dimethoxy-5-methyl-tetrahydro-pyran (123444-74-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 84 percent / Ph₃P, DIAD / tetrahydrofuran

2: 89 percent / imidazole / DMAP / dimethylformamide / 70 °C

3: 96 percent / DIBAL-H / CH₂Cl₂ / -78 °C

4: RuCl₃, NaIO₄ / CCl₄; acetonitrile; H₂O

5: K₂CO₃ / dimethylformamide

6: 1.) n-butyllithium / 1.) THF, -78 deg C, 10 min, 2.) 0 deg C, 1 h

7: 84 percent / tri-n-butyltin hydride, AIBN / toluene / Heating

8: 92 percent / HF-pyridine / tetrahydrofuran

9: acetic acid; acetonitrile / 18 h / -40 °C

10: 76 percent / NaH / dimethylformamide

With 1H-imidazole; ruthenium trichloride; sodium periodate; n-butyllithium; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; pyridine hydrogenfluoride; triphenylphosphine; dmap; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4039(01)80352-X

upstream raw materials:

methyl iodide

methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methylene-α-D-erythro-hexopyranoside

(2R,3S,5R,6S)-2-Hydroxymethyl-6-methoxy-5-methyl-tetrahydro-pyran-3-ol

[(2R,3S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-5-methyl-tetrahydro-pyran-2-yl]-methanol

Downstream raw materials:

Toluene-4-sulfonic acid (E)-(2S,6S,8S)-2-((S)-2,2-diisopropyl-[1,3]dioxolan-4-yl)-8-((2R,3S,5R,6S)-3,6-dimethoxy-5-methyl-tetrahydro-pyran-2-yl)-8-methoxy-4,6-dimethyl-oct-3-enyl ester