(2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-[(2S,3S,5R,6R)-5-benzyloxy-6-benzyloxymethyl-2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-3-ylmethyl]-6-methyl-tetrahydro-pyran

Base Information

• Chemical Name: (2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-[(2S,3S,5R,6R)-5-benzyloxy-6-benzyloxymethyl-2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-3-ylmethyl]-6-methyl-tetrahydro-pyran
• CAS No.: 138061-64-0
• Molecular Formula: C₆₉H₇₈O₁₁
• Molecular Weight: 1083.37
• Mol file: 138061-64-0.mol

Synonyms:

Chemical Property of (2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-[(2S,3S,5R,6R)-5-benzyloxy-6-benzyloxymethyl-2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-3-ylmethyl]-6-methyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-[(2S,3S,5R,6R)-5-benzyloxy-6-benzyloxymethyl-2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-3-ylmethyl]-6-methyl-tetrahydro-pyran

There total 25 articles about (2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-[(2S,3S,5R,6R)-5-benzyloxy-6-benzyloxymethyl-2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-3-ylmethyl]-6-methyl-tetrahydro-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:

2-((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethanol (138061-61-7) → (2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-[(2S,3S,5R,6R)-5-benzyloxy-6-benzyloxymethyl-2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-3-ylmethyl]-6-methyl-tetrahydro-pyran (138061-64-0)

Guidance literature:

Multi-step reaction with 15 steps

1: Swern oxidation

2: tetrahydrofuran; dibutyl ether / 0.33 h / Ambient temperature

3: Swern oxidation

4: 1.) lithium hexamethyldisilazane / 1.) toluene, hexanes, -78 deg C, 20 min, 2.) 20 min

5: 1.) TBAF*3H₂O, 2.) BF₃*OEt₂ / 1.) THF, r.t., 2.) methylene chloride, -15 deg C

6: 79 percent / tributyltin hydride, AIBN / toluene / 0.5 h / 110 °C

7: 91 percent / Swern oxidation

8: 1a.) lithium hexamethyldisilazane, TMEDA, 1b.) MgBr₂ / 1a.) THF, hexanes, -78 deg C, 35 min, 1b.) -78 deg C, 5 min, 2.) -78 deg C, 20 min

9: triethylamine / diethyl ether / 0.5 h / 0 °C

10: NH₃ / tetrahydrofuran / 0.5 h / -78 deg C to r.t.

11: 73 percent / tributyltin hydride, AIBN / benzene / 10 h / Heating

12: 85 percent / sodium borohydride / methanol / 0.5 h / 0 °C

13: 1.) NaH / 1.) THF, 0 deg C, 15 min, 2.) 1 h

14: tetrahydrofuran / 1 h

15: tributyltin hydride, AIBN / toluene / 0.17 h / Heating

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonia; tri-n-butyl-tin hydride; sodium hydride; triethylamine; magnesium bromide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dibutyl ether; toluene; benzene;

DOI:10.1021/jo00028a019

Reference yield:

1-((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-propan-2-one (138061-68-4) → (2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-[(2S,3S,5R,6R)-5-benzyloxy-6-benzyloxymethyl-2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-3-ylmethyl]-6-methyl-tetrahydro-pyran (138061-64-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) lithium hexamethyldisilazane / 1.) toluene, hexanes, -78 deg C, 20 min, 2.) 20 min

2: 1.) TBAF*3H₂O, 2.) BF₃*OEt₂ / 1.) THF, r.t., 2.) methylene chloride, -15 deg C

3: 79 percent / tributyltin hydride, AIBN / toluene / 0.5 h / 110 °C

4: 91 percent / Swern oxidation

5: 1a.) lithium hexamethyldisilazane, TMEDA, 1b.) MgBr₂ / 1a.) THF, hexanes, -78 deg C, 35 min, 1b.) -78 deg C, 5 min, 2.) -78 deg C, 20 min

6: triethylamine / diethyl ether / 0.5 h / 0 °C

7: NH₃ / tetrahydrofuran / 0.5 h / -78 deg C to r.t.

8: 73 percent / tributyltin hydride, AIBN / benzene / 10 h / Heating

9: 85 percent / sodium borohydride / methanol / 0.5 h / 0 °C

10: 1.) NaH / 1.) THF, 0 deg C, 15 min, 2.) 1 h

11: tetrahydrofuran / 1 h

12: tributyltin hydride, AIBN / toluene / 0.17 h / Heating

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonia; tri-n-butyl-tin hydride; sodium hydride; triethylamine; magnesium bromide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; toluene; benzene;

DOI:10.1021/jo00028a019

Reference yield:

((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-acetaldehyde → (2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-[(2S,3S,5R,6R)-5-benzyloxy-6-benzyloxymethyl-2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-3-ylmethyl]-6-methyl-tetrahydro-pyran (138061-64-0)

Guidance literature:

Multi-step reaction with 14 steps

1: tetrahydrofuran; dibutyl ether / 0.33 h / Ambient temperature

2: Swern oxidation

3: 1.) lithium hexamethyldisilazane / 1.) toluene, hexanes, -78 deg C, 20 min, 2.) 20 min

4: 1.) TBAF*3H₂O, 2.) BF₃*OEt₂ / 1.) THF, r.t., 2.) methylene chloride, -15 deg C

5: 79 percent / tributyltin hydride, AIBN / toluene / 0.5 h / 110 °C

6: 91 percent / Swern oxidation

7: 1a.) lithium hexamethyldisilazane, TMEDA, 1b.) MgBr₂ / 1a.) THF, hexanes, -78 deg C, 35 min, 1b.) -78 deg C, 5 min, 2.) -78 deg C, 20 min

8: triethylamine / diethyl ether / 0.5 h / 0 °C

9: NH₃ / tetrahydrofuran / 0.5 h / -78 deg C to r.t.

10: 73 percent / tributyltin hydride, AIBN / benzene / 10 h / Heating

11: 85 percent / sodium borohydride / methanol / 0.5 h / 0 °C

12: 1.) NaH / 1.) THF, 0 deg C, 15 min, 2.) 1 h

13: tetrahydrofuran / 1 h

14: tributyltin hydride, AIBN / toluene / 0.17 h / Heating

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonia; tri-n-butyl-tin hydride; sodium hydride; triethylamine; magnesium bromide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dibutyl ether; toluene; benzene;

DOI:10.1021/jo00028a019

upstream raw materials:

2-((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethanol

1-((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-propan-2-one

(2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

Refernces