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

Base Information

• Chemical Name: (2S,3R,5R)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone
• CAS No.: 506423-05-8
• Molecular Formula: C₂₆H₃₆O₄Si
• Molecular Weight: 440.655
• Mol file: 506423-05-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (2S,3R,5R)-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:

C20H22O4 (506423-04-7) + C20H22O4 (544673-43-0) + tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone (506423-06-9) + (2S,3R,5R)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone (506423-05-8)

Guidance literature:

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

Reference yield:

(2R,3S,4R,6S)-3,4-diacetoxy-2-(acetoxymethyl)-6-methoxytetrahydro-2H-pyran (6087-40-7) → (2S,3R,5R)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone (506423-05-8)

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:

Methyl 3,4-di-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside (145149-85-5) → (2S,3R,5R)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone (506423-05-8)

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

upstream raw materials:

tert-butyldimethylsilyl chloride

(2S,3R)-2,3-Bis-benzyloxy-5-hydroxy-cyclohexanone

(2R,3S,4R,6S)-3,4-diacetoxy-2-(acetoxymethyl)-6-methoxytetrahydro-2H-pyran

Methyl 3,4-di-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside