(2S,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone

Base Information

Chemical Name:(2S,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone
CAS No.:506423-06-9
Molecular Formula:C₂₆H₃₆O₄Si
Molecular Weight:440.655
Hs Code.:

Synonyms:(2S,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone

Chemical Property:

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Technology Process of (2S,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone

There total 9 articles about (2S,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone 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:

: 506423-04-7
C₂₀H₂₂O₄

: 544673-43-0
C₂₀H₂₂O₄

: 18162-48-6
tert-butyldimethylsilyl chloride

: 506423-06-9
(2S,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone

: 506423-05-8
(2S,3R,5R)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone

Guidance literature:: With 1H-imidazole; In DMF (N,N-dimethyl-formamide); at 0 - 20 ℃; for 5h;

Reference yield:

: 6087-40-7
(2R,3S,4R,6S)-3,4-diacetoxy-2-(acetoxymethyl)-6-methoxytetrahydro-2H-pyran

: 506423-06-9
(2S,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone

Guidance literature:: Multi-step reaction with 8 steps

1: NaOMe; MeOH

2: pTsOH

3: 90 percent / dimethylformamide

4: 84 percent / LiAlH₄; AlCl₃ / diethyl ether

5: 82 percent / I₂; PPh₃ / tetrahydrofuran

6: 95 percent / AgF; pyridine

7: 92 percent / PdCl₂; H₂O / dioxane / 60 °C

8: dimethylformamide

With pyridine; methanol; lithium aluminium tetrahydride; aluminium trichloride; water; iodine; sodium methylate; silver fluoride; toluene-4-sulfonic acid; triphenylphosphine; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(03)00005-2

Reference yield:

: 145149-85-5
Methyl 3,4-di-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside

: 506423-06-9
(2S,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / I₂; PPh₃ / tetrahydrofuran

2: 95 percent / AgF; pyridine

3: 92 percent / PdCl₂; H₂O / dioxane / 60 °C

4: dimethylformamide

With pyridine; water; iodine; silver fluoride; triphenylphosphine; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(03)00005-2