(2R,3S,6S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-((Z)-((3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ylidene)methyl)-3,6-dihydro-2H-pyran

Base Information

• Chemical Name: (2R,3S,6S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-((Z)-((3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ylidene)methyl)-3,6-dihydro-2H-pyran
• CAS No.: 1462962-15-7
• Molecular Formula: C₆₂H₆₂O₉
• Molecular Weight: 951.169
• Mol file: 1462962-15-7.mol

Synonyms:(2R,3S,6S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-((Z)-((3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ylidene)methyl)-3,6-dihydro-2H-pyran

Chemical Property of (2R,3S,6S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-((Z)-((3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ylidene)methyl)-3,6-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,6S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-((Z)-((3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ylidene)methyl)-3,6-dihydro-2H-pyran

There total 3 articles about (2R,3S,6S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-((Z)-((3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ylidene)methyl)-3,6-dihydro-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: 87.0%

3,4,6-tri-O-benzyl-D-galactal (80040-79-5) + (2R,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran (607715-91-3) → (2R,3S,6S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-((Z)-((3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ylidene)methyl)-3,6-dihydro-2H-pyran (1462962-15-7)

Guidance literature:

With 1,3-bis-(diphenylphosphino)propane; tetrabutyl-ammonium chloride; palladium diacetate; potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 3h;

DOI:10.1016/j.tetlet.2013.08.118

Reference yield:

(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one (179090-11-0) → (2R,3S,6S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-((Z)-((3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ylidene)methyl)-3,6-dihydro-2H-pyran (1462962-15-7)

Guidance literature:

Multi-step reaction with 2 steps

1: bis(2,4,6-trimethylphenyl)iodonium triflate / dichloromethane / 20 °C

2: tetrabutyl-ammonium chloride; potassium carbonate; palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 3 h / 80 °C

With 1,3-bis-(diphenylphosphino)propane; tetrabutyl-ammonium chloride; palladium diacetate; potassium carbonate; bis(2,4,6-trimethylphenyl)iodonium triflate; In dichloromethane; N,N-dimethyl-formamide; 2: |Heck Reaction;

DOI:10.1016/j.tetlet.2013.08.118

Reference yield:

2,3,4,6-tetra-O-benzyl-D-galactonolactone (82598-84-3) → (2R,3S,6S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-((Z)-((3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ylidene)methyl)-3,6-dihydro-2H-pyran (1462962-15-7)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene / 75 °C

2: bis(2,4,6-trimethylphenyl)iodonium triflate / dichloromethane / 20 °C

3: tetrabutyl-ammonium chloride; potassium carbonate; palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 3 h / 80 °C

With 1,3-bis-(diphenylphosphino)propane; tetrabutyl-ammonium chloride; palladium diacetate; potassium carbonate; bis(2,4,6-trimethylphenyl)iodonium triflate; In dichloromethane; N,N-dimethyl-formamide; toluene; 3: |Heck Reaction;

DOI:10.1016/j.tetlet.2013.08.118

upstream raw materials:

3,4,6-tri-O-benzyl-D-galactal

(2R,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran

2,3,4,6-tetra-O-benzyl-D-galactonolactone

(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one