(3R,5R)-3,5-bis<(tert-butyldimethylsilyl)oxy>-4-<(trimethylsilyl)oxy>cyclohexanone

Base Information

Chemical Name:(3R,5R)-3,5-bis<(tert-butyldimethylsilyl)oxy>-4-<(trimethylsilyl)oxy>cyclohexanone
CAS No.:141404-09-3
Molecular Formula:C₂₁H₄₆O₄Si₃
Molecular Weight:446.85
Hs Code.:

Synonyms:(3R,5R)-3,5-bis<(tert-butyldimethylsilyl)oxy>-4-<(trimethylsilyl)oxy>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 (3R,5R)-3,5-bis<(tert-butyldimethylsilyl)oxy>-4-<(trimethylsilyl)oxy>cyclohexanone

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Technology Process of (3R,5R)-3,5-bis<(tert-butyldimethylsilyl)oxy>-4-<(trimethylsilyl)oxy>cyclohexanone

There total 15 articles about (3R,5R)-3,5-bis<(tert-butyldimethylsilyl)oxy>-4-<(trimethylsilyl)oxy>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: 99.0%

: 18156-74-6
1-(Trimethylsilyl)imidazole

: 141404-08-2
(3R,5R)-3,5-bis[tert-butyl(dimethyl)silyloxy]-4-hydroxycyclohexanone

: 141404-09-3
(3R,5R)-3,5-bis<(tert-butyldimethylsilyl)oxy>-4-<(trimethylsilyl)oxy>cyclohexanone

Guidance literature:: In dichloromethane;
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

: 141404-09-3
(3R,5R)-3,5-bis<(tert-butyldimethylsilyl)oxy>-4-<(trimethylsilyl)oxy>cyclohexanone

Guidance literature:: Multi-step reaction with 15 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

10: 94 percent / dimethylformamide

11: 95 percent / Bu₄NF / tetrahydrofuran

12: 98 percent / (COCl)2; DMSO / CH₂Cl₂

13: H₂ / Pd/C / ethanol

14: dimethylformamide

15: 99 percent / CH₂Cl₂

With pyridine; methanol; lithium aluminium tetrahydride; aluminium trichloride; oxalyl dichloride; tetrabutyl ammonium fluoride; water; hydrogen; iodine; sodium methylate; silver fluoride; L-Selectride; toluene-4-sulfonic acid; dimethyl sulfoxide; triphenylphosphine; palladium dichloride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; 12: Swern oxidation;
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

: 141404-09-3
(3R,5R)-3,5-bis<(tert-butyldimethylsilyl)oxy>-4-<(trimethylsilyl)oxy>cyclohexanone

Guidance literature:: Multi-step reaction with 11 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

6: 94 percent / dimethylformamide

7: 95 percent / Bu₄NF / tetrahydrofuran

8: 98 percent / (COCl)2; DMSO / CH₂Cl₂

9: H₂ / Pd/C / ethanol

10: dimethylformamide

11: 99 percent / CH₂Cl₂

With pyridine; oxalyl dichloride; tetrabutyl ammonium fluoride; water; hydrogen; iodine; silver fluoride; L-Selectride; dimethyl sulfoxide; triphenylphosphine; palladium dichloride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; 8: Swern oxidation;
DOI:10.1016/S0960-894X(03)00005-2