(2R,4R,6S)-(E)-6-<2-(4'-fluoro,3,3',5-trimethyl<1,1'-biphenyl>-2-yl)ethenyl>-4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran

Base Information

• Chemical Name: (2R,4R,6S)-(E)-6-<2-(4'-fluoro,3,3',5-trimethyl<1,1'-biphenyl>-2-yl)ethenyl>-4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran
• CAS No.: 100295-49-6
• Molecular Formula: C₃₀H₃₃FO₃
• Molecular Weight: 460.589
• Mol file: 100295-49-6.mol

Synonyms:

Chemical Property of (2R,4R,6S)-(E)-6-<2-(4'-fluoro,3,3',5-trimethyl<1,1'-biphenyl>-2-yl)ethenyl>-4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,6S)-(E)-6-<2-(4'-fluoro,3,3',5-trimethyl<1,1'-biphenyl>-2-yl)ethenyl>-4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran

There total 19 articles about (2R,4R,6S)-(E)-6-<2-(4'-fluoro,3,3',5-trimethyl<1,1'-biphenyl>-2-yl)ethenyl>-4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran 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:

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-ribo-hexopyranoside (63592-79-0) → (2R,4R,6S)-(E)-6-<2-(4'-fluoro,3,3',5-trimethyl<1,1'-biphenyl>-2-yl)ethenyl>-4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran (100295-49-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 88 percent / aq. trifluoroacetic acid / CH₂Cl₂ / 0.17 h

2: 86 percent / pyridine / 144 h

3: 89.5 percent / pyridine / Ambient temperature

4: 83.5 percent / 70percent aq. trifluoroacetic acid / CH₂Cl₂ / 0.08 h

5: 81.3 percent / NaBH₄ / dimethylsulfoxide / 96 h / 80 °C

6: 77.5 percent / pyridine / 4 h / Ambient temperature

7: 86 percent / NaI / acetone / 24 h / Heating

8: 1.) NaH / 1.) DMSO, RT, 10 min, 2.) DMSO, RT, 1 h

9: 85 percent / K₂CO₃ / toluene / 3 h / 90 °C

10: 1.) ethanol, 2.) aq.AcOH / 1.) 20percent Pd(OH)2/C / 1.) reflux, 100 h, 2.) RT, 30 h

11: 56.7 percent / N-iodosuccinimide, tetra-n-butylammonium iodide / CH₂Cl₂ / 2 h

12: 1.) diisobutyl aluminium hydride, 2.) AcOH / 1.) THF, toluene, -78 deg C, 2.) 24 h

13: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, DMF, 50 deg C, 2 h

With pyridine; sodium tetrahydroborate; N-iodo-succinimide; n-butyllithium; ethanol; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; trifluoroacetic acid; sodium iodide; palladium dihydroxide; In dichloromethane; dimethyl sulfoxide; acetone; toluene;

DOI:10.1021/jo00355a014

Reference yield:

methyl 3-O-benzyl-4-O-tosyl-2-deoxy-α-D-ribo-hexopyranoside (82300-41-2) → (2R,4R,6S)-(E)-6-<2-(4'-fluoro,3,3',5-trimethyl<1,1'-biphenyl>-2-yl)ethenyl>-4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran (100295-49-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 81.3 percent / NaBH₄ / dimethylsulfoxide / 96 h / 80 °C

2: 77.5 percent / pyridine / 4 h / Ambient temperature

3: 86 percent / NaI / acetone / 24 h / Heating

4: 1.) NaH / 1.) DMSO, RT, 10 min, 2.) DMSO, RT, 1 h

5: 85 percent / K₂CO₃ / toluene / 3 h / 90 °C

6: 1.) ethanol, 2.) aq.AcOH / 1.) 20percent Pd(OH)2/C / 1.) reflux, 100 h, 2.) RT, 30 h

7: 56.7 percent / N-iodosuccinimide, tetra-n-butylammonium iodide / CH₂Cl₂ / 2 h

8: 1.) diisobutyl aluminium hydride, 2.) AcOH / 1.) THF, toluene, -78 deg C, 2.) 24 h

9: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, DMF, 50 deg C, 2 h

With pyridine; sodium tetrahydroborate; N-iodo-succinimide; n-butyllithium; ethanol; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; sodium iodide; palladium dihydroxide; In dichloromethane; dimethyl sulfoxide; acetone; toluene;

DOI:10.1021/jo00355a014

Reference yield:

methyl 3-O-benzyl-2-deoxy-α-D-ribo-hexopyranoside (64951-98-0) → (2R,4R,6S)-(E)-6-<2-(4'-fluoro,3,3',5-trimethyl<1,1'-biphenyl>-2-yl)ethenyl>-4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran (100295-49-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 86 percent / pyridine / 144 h

2: 89.5 percent / pyridine / Ambient temperature

3: 83.5 percent / 70percent aq. trifluoroacetic acid / CH₂Cl₂ / 0.08 h

4: 81.3 percent / NaBH₄ / dimethylsulfoxide / 96 h / 80 °C

5: 77.5 percent / pyridine / 4 h / Ambient temperature

6: 86 percent / NaI / acetone / 24 h / Heating

7: 1.) NaH / 1.) DMSO, RT, 10 min, 2.) DMSO, RT, 1 h

8: 85 percent / K₂CO₃ / toluene / 3 h / 90 °C

9: 1.) ethanol, 2.) aq.AcOH / 1.) 20percent Pd(OH)2/C / 1.) reflux, 100 h, 2.) RT, 30 h

10: 56.7 percent / N-iodosuccinimide, tetra-n-butylammonium iodide / CH₂Cl₂ / 2 h

11: 1.) diisobutyl aluminium hydride, 2.) AcOH / 1.) THF, toluene, -78 deg C, 2.) 24 h

12: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, DMF, 50 deg C, 2 h

With pyridine; sodium tetrahydroborate; N-iodo-succinimide; n-butyllithium; ethanol; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; trifluoroacetic acid; sodium iodide; palladium dihydroxide; In dichloromethane; dimethyl sulfoxide; acetone; toluene;

DOI:10.1021/jo00355a014

upstream raw materials:

benzyl bromide

(2R,4R,6S)-(E)-6-<2-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)ethenyl>-4-hydroxy-2-methoxy-3,4,5,6-tetrahydro-2H-pyran

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-ribo-hexopyranoside

methyl 3-O-benzyl-4-O-tosyl-2-deoxy-α-D-ribo-hexopyranoside

Refernces