(S)-2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohexanone

Base Information

• Chemical Name: (S)-2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohexanone
• CAS No.: 892867-42-4
• Molecular Formula: C₄₅H₅₈O₄Si
• Molecular Weight: 691.039
• Mol file: 892867-42-4.mol

Synonyms:(S)-2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohexanone

Chemical Property of (S)-2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohexanone

There total 9 articles about (S)-2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-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: 77.0%

2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohex-2-enone (892867-41-3) → (S)-2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohexanone (892867-42-4) + (R)-2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohexanone (892867-43-5)

Guidance literature:

With sodium tetrahydroborate; nickel dichloride; In methanol; dichloromethane; at 0 ℃; for 0.166667h;

DOI:10.1016/j.tetlet.2006.03.078

Reference yield: 60.0%

(R)-2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohexanone (892867-43-5) → (S)-2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohexanone (892867-42-4)

Guidance literature:

With potassium hydroxide; In methanol; at 60 ℃; for 2h;

DOI:10.1016/j.tetlet.2006.03.078

Reference yield:

(3S,4S,5S)-3,4-Dimethyl-5-trityloxymethyl-dihydro-furan-2-one → (S)-2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohexanone (892867-42-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: LDA / tetrahydrofuran / 0.17 h / -78 °C

1.2: 91 percent / SOCl₂; pyridine / 1 h / 0 °C

2.1: LiBH₄ / tetrahydrofuran / 38 h / 65 °C

3.1: K₂CO₃; 18-crown-6-ether / acetonitrile / 8 h / 50 °C

4.1: DBU / acetonitrile / 20 h / 65 °C

5.1: 86 percent / SeO₂ / dioxane; H₂O / 17 h / 90 °C

6.1: 77 percent / NaBH₄; NiCl₂*6H₂O / methanol; CH₂Cl₂ / 0.17 h / 0 °C

With sodium tetrahydroborate; lithium borohydride; selenium(IV) oxide; 18-crown-6 ether; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; nickel dichloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetonitrile;

DOI:10.1016/j.tetlet.2006.03.078

upstream raw materials:

2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohex-2-enone

(R)-2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohexanone

(3R,4S,5S)-3-Cyclohex-1-enyl-3,4-dimethyl-5-trityloxymethyl-dihydro-furan-2-one

(2R,3S,4S)-2-Cyclohex-1-enyl-2,3-dimethyl-5-trityloxy-pentane-1,4-diol

Downstream raw materials:

(3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-ol

(1R,2S,3S,4R,4aS,8aS)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-3,4-dimethyl-octahydro-naphthalene-1,8a-diol

(E)-2-((3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-yloxy)-but-2-enedioic acid diethyl ester

(-)-tetrodecamycin