(1R,2S,6R,7R,9S)-(+)-9-(tert-butyldiphenylsilyloxy)-6-<(1S,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

Base Information

• Chemical Name: (1R,2S,6R,7R,9S)-(+)-9-(tert-butyldiphenylsilyloxy)-6-<(1S,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
• CAS No.: 126267-16-1
• Molecular Formula: C₃₇H₅₅NO₇Si₂
• Molecular Weight: 682.017
• Mol file: 126267-16-1.mol

Synonyms:

Chemical Property of (1R,2S,6R,7R,9S)-(+)-9-(tert-butyldiphenylsilyloxy)-6-<(1S,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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,6R,7R,9S)-(+)-9-(tert-butyldiphenylsilyloxy)-6-<(1S,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

There total 54 articles about (1R,2S,6R,7R,9S)-(+)-9-(tert-butyldiphenylsilyloxy)-6-<(1S,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 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: 32.0%

tert-Butyl-dimethyl-((Z)-2-tributylstannanylmethyl-but-2-enyloxy)-silane (102615-85-0) + (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) → (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<7.3.1.02.7>tridecan-11-one (126267-16-1,138876-90-1,138876-92-3,138921-37-6,141521-42-8,141554-53-2,141554-54-3,141554-55-4) + (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<7.3.1.02.7>tridecan-11-one (126267-16-1,138876-90-1,138876-92-3,138921-37-6,141521-42-8,141554-53-2,141554-54-3,141554-55-4)

Guidance literature:

With boron trifluoride diethyl etherate; triethylamine; In dichloromethane; at -78 ℃; for 3h;

Reference yield: 32.0%

tert-Butyl-dimethyl-((Z)-2-tributylstannanylmethyl-but-2-enyloxy)-silane (102615-85-0) + (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) → (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<7.3.1.02.7>tridecan-11-one (126267-16-1,138876-90-1,138876-92-3,138921-37-6,141521-42-8,141554-53-2,141554-54-3,141554-55-4) + (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<7.3.1.02.7>tridecan-11-one (126267-16-1,138876-90-1,138876-92-3,138921-37-6,141521-42-8,141554-53-2,141554-54-3,141554-55-4)

Guidance literature:

With boron trifluoride diethyl etherate; triethylamine; In dichloromethane; at -78 ℃; for 3h;

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-<(1S,2S)-1-hydroxy-2-methyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.02.7>tridecan-11-one (126267-16-1,138876-90-1,138876-92-3,138921-37-6,141521-42-8,141554-53-2,141554-54-3,141554-55-4)

Guidance literature:

Multi-step reaction with 9 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

9: 30 percent / Et₃N / Cl₃TiOiPr / CH₂Cl₂ / a) -78 deg C, 15 min, b) to -65 to -60 deg C, 6 h

With pyridine; 2,3,5-trimethyl-pyridine; hydrogenchloride; hydrogen; diisobutylaluminium hydride; triethylamine; benzoic acid; palladium on activated charcoal; titanium(IV) trichloride isopropoxide; In tetrahydrofuran; methanol; dichloromethane; toluene;

upstream raw materials:

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

tert-butyldiphenylsilyl triflate

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

(E,4S,5R,6R)-methyl 5,7-di(benzyloxy)-4,6-dihydroxy-2-heptenoate

Downstream raw materials:

(+/-)-sesbanimide A

(+/-)-sesbanimide B

(+)-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