(2S,3R,4S,5R,6R)-2-methoxy-6-((((2S,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate

Base Information

• Chemical Name: (2S,3R,4S,5R,6R)-2-methoxy-6-((((2S,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• CAS No.: 190515-39-0
• Molecular Formula: C₆₂H₆₀O₁₄
• Molecular Weight: 1029.15

Synonyms:(2S,3R,4S,5R,6R)-2-methoxy-6-((((2S,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate

Chemical Property of (2S,3R,4S,5R,6R)-2-methoxy-6-((((2S,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate

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Technology Process of (2S,3R,4S,5R,6R)-2-methoxy-6-((((2S,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate

There total 19 articles about (2S,3R,4S,5R,6R)-2-methoxy-6-((((2S,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 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: 30.0%

methyl 2,3,4-tri-O-benzoylglucopyranoside (34234-44-1) + phenyl-2,3,4,6-tetra-O-benzyl-1-seleno-β-D-galactopyrannoside (139903-48-3,139903-49-4,143995-67-9) → 2,3,4,6-tetra-O-benzyl-D-galactopyranose (6386-24-9) + (2S,3R,4S,5R,6R)-2-methoxy-6-((((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (194471-78-8) + (2S,3R,4S,5R,6R)-2-methoxy-6-((((2S,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (190515-39-0)

Guidance literature:

With oxygen; N-methyl-1-quinolinium hexafluorophosphate; In toluene; acetonitrile; at 20 ℃; optical yield given as %de; diastereoselective reaction; Molecular sieve; UV-irradiation; Air atmosphere;

DOI:10.1080/07328303.2011.601533

Reference yield:

methyl 2,3,4-tri-O-benzoylglucopyranoside (34234-44-1) + phenyl (2,3,4,6-tetra-O-benzyl)-1-thio-β-D-galactopyranoside S-oxide (117307-18-3) → (2S,3R,4S,5R,6R)-2-methoxy-6-((((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (194471-78-8) + (2S,3R,4S,5R,6R)-2-methoxy-6-((((2S,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (190515-39-0)

Guidance literature:

With gold(III) chloride; silver trifluoromethanesulfonate; In dichloromethane; at 35 - 39 ℃; for 0.583333h; Overall yield = 80 %; Overall yield = 127 mg; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.carres.2016.11.012

Reference yield:

methyl 2,3,4-tri-O-benzoylglucopyranoside (34234-44-1) + propargyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside → (2S,3R,4S,5R,6R)-2-methoxy-6-((((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (194471-78-8) + (2S,3R,4S,5R,6R)-2-methoxy-6-((((2S,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (190515-39-0)

Guidance literature:

With iron(III) chloride; In acetonitrile; at 60 ℃; for 15h; Overall yield = 84 %; Inert atmosphere; Green chemistry;

DOI:10.1055/s-0036-1591525

upstream raw materials:

methyl 2,3,4-tri-O-benzoylglucopyranoside

ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside

phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside

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

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