(1R,2R,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol

Base Information

Chemical Name:(1R,2R,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol
CAS No.:506423-07-0
Molecular Formula:C₂₆H₃₈O₄Si
Molecular Weight:442.671
Hs Code.:

Synonyms:(1R,2R,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol

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Chemical Property of (1R,2R,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol

Chemical Property:

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Technology Process of (1R,2R,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol

There total 9 articles about (1R,2R,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol 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: 95.0%

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

: 506423-07-0
(1R,2R,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol

Guidance literature:: With L-Selectride; In tetrahydrofuran;
DOI:10.1016/S0960-894X(03)00005-2

Reference yield:

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

: 506423-07-0
(1R,2R,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol

Guidance literature:: Multi-step reaction with 9 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

9: 95 percent / L-Selectride / tetrahydrofuran

With pyridine; methanol; lithium aluminium tetrahydride; aluminium trichloride; water; iodine; sodium methylate; silver fluoride; L-Selectride; 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

: 506423-07-0
(1R,2R,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / I₂; PPh₃ / tetrahydrofuran

2: 95 percent / AgF; pyridine

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

4: dimethylformamide

5: 95 percent / L-Selectride / tetrahydrofuran

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