(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
Hs Code.:

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

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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

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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%

: 123444-72-4
(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

: 123444-73-5
(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

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran;
DOI:10.1016/S0040-4039(01)80352-X

Reference yield:

: 35905-41-0
methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methylene-α-D-erythro-hexopyranoside

: 123444-73-5
(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

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:

: 123474-66-8
(2R,3S,5R,6S)-2-Hydroxymethyl-6-methoxy-5-methyl-tetrahydro-pyran-3-ol

: 123444-73-5
(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

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