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

Base Information

• Chemical Name: (E)-(3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-((2S,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-3,5-dimethyl-non-5-en-1-one
• CAS No.: 123444-73-5
• Molecular Formula: C₄₀H₅₂O₇
• Molecular Weight: 644.849
• Mol file: 123444-73-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about (E)-(3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-((2S,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-3,5-dimethyl-non-5-en-1-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: 92.0%

(E)-(3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-[(2S,3S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3,5-dimethyl-non-5-en-1-one (123444-72-4) → (E)-(3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-((2S,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-3,5-dimethyl-non-5-en-1-one (123444-73-5)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran;

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) → (E)-(3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-((2S,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-3,5-dimethyl-non-5-en-1-one (123444-73-5)

Guidance literature:

Multi-step reaction with 10 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

With 1H-imidazole; ruthenium trichloride; sodium periodate; n-butyllithium; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; potassium carbonate; pyridine hydrogenfluoride; triphenylphosphine; dmap; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; water; 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) → (E)-(3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-((2S,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-3,5-dimethyl-non-5-en-1-one (123444-73-5)

Guidance literature:

Multi-step reaction with 8 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

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

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

upstream raw materials:

(E)-(3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-[(2S,3S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3,5-dimethyl-non-5-en-1-one

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:

(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