(1R,2S,6S,7R,9S)-9-(tert-Butyl-diphenyl-silanyloxy)-11-oxo-3,5,8-trioxa-10-aza-tricyclo[7.3.1.0^2,7]tridecane-6-carbaldehyde

Base Information

• Chemical Name: (1R,2S,6S,7R,9S)-9-(tert-Butyl-diphenyl-silanyloxy)-11-oxo-3,5,8-trioxa-10-aza-tricyclo[7.3.1.0^2,7]tridecane-6-carbaldehyde
• CAS No.: 126267-15-0
• Molecular Formula: C₂₆H₃₁NO₆Si
• Molecular Weight: 481.621
• Mol file: 126267-15-0.mol

Synonyms:

Chemical Property of (1R,2S,6S,7R,9S)-9-(tert-Butyl-diphenyl-silanyloxy)-11-oxo-3,5,8-trioxa-10-aza-tricyclo[7.3.1.0^2,7]tridecane-6-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,6S,7R,9S)-9-(tert-Butyl-diphenyl-silanyloxy)-11-oxo-3,5,8-trioxa-10-aza-tricyclo[7.3.1.0^2,7]tridecane-6-carbaldehyde

There total 24 articles about (1R,2S,6S,7R,9S)-9-(tert-Butyl-diphenyl-silanyloxy)-11-oxo-3,5,8-trioxa-10-aza-tricyclo[7.3.1.0^2,7]tridecane-6-carbaldehyde 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: 93.0%

(1R,2S,6R,7R,9S)-(-)-9-(tert-butyldiphenylsilyloxy)-6-(hydroxymethyl)-3,5,8-trioxa-10-azatricyclo<7.3.1.02,7>tridecan-11-one (126267-13-8,141554-51-0) → (1R,2S,6R,7R,9S)-(-)-9-(tert-butyldiphenylsilyloxy)-6-formyl-3,5,8-trioxa-10-azatricyclo<7.3.1.02,7>tridecan-11-one (126267-15-0,141554-52-1)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 7h; Dess-Martin periodinane reagent;

Reference yield: 90.0%

(1R,2S,6R,7R,9S)-9-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxymethyl-3,5,8-trioxa-10-aza-tricyclo[7.3.1.02,7]tridecan-11-one (126267-13-8,141554-51-0) → (1R,2S,6S,7R,9S)-9-(tert-Butyl-diphenyl-silanyloxy)-11-oxo-3,5,8-trioxa-10-aza-tricyclo[7.3.1.02,7]tridecane-6-carbaldehyde (126267-15-0,141554-52-1)

Guidance literature:

With dipyridine chromium trioxide; In dichloromethane; for 0.5h;

DOI:10.1039/c39920000368

Reference yield:

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (41341-99-5) → (1R,2S,6R,7R,9S)-(-)-9-(tert-butyldiphenylsilyloxy)-6-formyl-3,5,8-trioxa-10-azatricyclo<7.3.1.02,7>tridecan-11-one (126267-15-0,141554-52-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 30percent HCl / tetrahydrofuran / 2 h / 20 °C

2: benzoic acid / toluene / 29 h / 22 °C

3: toluene, reflux, 30 min

4: H₂ / Pd/C / methanol

5: 94 percent / pyridine / 60 h / -10 °C

6: 90 percent / collidine / CH₂Cl₂ / 24 h / Ambient temperature

7: 84 percent / DIBAH / tetrahydrofuran / -78 °C

8: 93 percent / pyridine / CH₂Cl₂ / 7 h / 20 °C / Dess-Martin periodinane reagent

With pyridine; 2,3,5-trimethyl-pyridine; hydrogenchloride; hydrogen; diisobutylaluminium hydride; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene;

upstream raw materials:

(1R,2S,6R,7R,9S)-(-)-9-(tert-butyldiphenylsilyloxy)-6-(hydroxymethyl)-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2,7>tridecan-11-one

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

tert-butyldiphenylsilyl triflate

3,5-di-O-benzyl-D-xylofuranose

Downstream raw materials:

(1R,2S,6R,7R,9S)-(-)-9-(tert-butyldiphenylsilyloxy)-6-<(1R,2R)-1-hydroxy-2-methyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2.7>tridecan-11-one

(1R,2S,6R,7R,9S)-(-)-9-(tert-butyldiphenylsilyloxy)-6-<(1R,2S)-1-hydroxy-2-methyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2.7>tridecan-11-one

(+)-sesbanimide A

(1R,2S,6R,9S)-(-)-9-(tert-butyldiphenylsilyloxy)-6-<(2R)-1-oxo-2-methyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2,7>tridecan-11-one