(2R,3S,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-[1-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-meth-(Z)-ylidene]-tetrahydro-pyran-4-one

Base Information

• Chemical Name: (2R,3S,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-[1-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-meth-(Z)-ylidene]-tetrahydro-pyran-4-one
• CAS No.: 138061-74-2
• Molecular Formula: C₆₉H₇₄O₁₂
• Molecular Weight: 1095.34
• Mol file: 138061-74-2.mol

Synonyms:

Chemical Property of (2R,3S,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-[1-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-meth-(Z)-ylidene]-tetrahydro-pyran-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-[1-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-meth-(Z)-ylidene]-tetrahydro-pyran-4-one

There total 20 articles about (2R,3S,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-[1-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-meth-(Z)-ylidene]-tetrahydro-pyran-4-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:

2-((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethanol (138061-61-7) → (2R,3S,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-[1-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-meth-(Z)-ylidene]-tetrahydro-pyran-4-one (138061-74-2,138230-77-0)

Guidance literature:

Multi-step reaction with 10 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.

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

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) → (2R,3S,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-[1-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-meth-(Z)-ylidene]-tetrahydro-pyran-4-one (138061-74-2,138230-77-0)

Guidance literature:

Multi-step reaction with 7 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.

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

DOI:10.1021/jo00028a019

Reference yield:

((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-acetaldehyde → (2R,3S,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-[1-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-meth-(Z)-ylidene]-tetrahydro-pyran-4-one (138061-74-2,138230-77-0)

Guidance literature:

Multi-step reaction with 9 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.

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

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

Downstream raw materials:

(2R,3S,5S,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-4-one

(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

(2R,3R,4R,5R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-4-ol