(E)-(3S,7S,8S)-2-Benzenesulfonyl-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

Base Information

Chemical Name:(E)-(3S,7S,8S)-2-Benzenesulfonyl-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
CAS No.:123465-13-4
Molecular Formula:C₅₂H₇₀O₉SSi
Molecular Weight:899.274
Hs Code.:

(E)-(3S,7S,8S)-2-Benzenesulfonyl-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

Synonyms:(E)-(3S,7S,8S)-2-Benzenesulfonyl-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

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Chemical Property of (E)-(3S,7S,8S)-2-Benzenesulfonyl-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

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Technology Process of (E)-(3S,7S,8S)-2-Benzenesulfonyl-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

There total 16 articles about (E)-(3S,7S,8S)-2-Benzenesulfonyl-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 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:

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

: 123465-13-4
(E)-(3S,7S,8S)-2-Benzenesulfonyl-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

Guidance literature:: Multi-step reaction with 8 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

With 1H-imidazole; ruthenium trichloride; sodium periodate; n-butyllithium; di-isopropyl azodicarboxylate; hydrogen; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; dmap; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 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

: 123465-13-4
(E)-(3S,7S,8S)-2-Benzenesulfonyl-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

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; ruthenium trichloride; sodium periodate; n-butyllithium; di-isopropyl azodicarboxylate; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; dmap; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(01)80352-X

Reference yield:

: 123444-64-4
Benzoic acid (2R,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

: 123465-13-4
(E)-(3S,7S,8S)-2-Benzenesulfonyl-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

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / imidazole / DMAP / dimethylformamide / 70 °C

2: 96 percent / DIBAL-H / CH₂Cl₂ / -78 °C

3: RuCl₃, NaIO₄ / CCl₄; acetonitrile; H₂O

4: K₂CO₃ / dimethylformamide

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

With 1H-imidazole; ruthenium trichloride; sodium periodate; n-butyllithium; diisobutylaluminium hydride; potassium carbonate; dmap; In tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(01)80352-X