(2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran

Base Information

• Chemical Name: (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran
• CAS No.: 122588-56-1
• Molecular Formula: C₂₉H₃₂O₅
• Molecular Weight: 460.57
• Mol file: 122588-56-1.mol

Synonyms:(2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran

Chemical Property of (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran

There total 15 articles about (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-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: 100.0%

methyl-2,3,4-tri-O-benzyl-7-(Si-dimethylphenyl-silyl)-L-glycero-α-Dmanno-heptopyranoside (122588-55-0) → (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran (122588-56-1)

Guidance literature:

With tetrafluoroboric acid; In dichloromethane;

DOI:10.1016/S0040-4039(00)95167-0

Reference yield: 60.0%

methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside (40653-15-4) + Methyltriphenylphosphonium bromide (1779-49-3) → (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran (122588-56-1)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at 15 ℃; for 0.5h; Inert atmosphere;

methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside; In tetrahydrofuran; at -78 - 20 ℃; for 18h;

With water; ammonium chloride; In tetrahydrofuran; diethyl ether;

Reference yield: 44.0%

methyl-2,3,4,6-tetra-O-benzyl-7-(dimethylphenyl-silyl)-L-glycero-α-Dmanno-heptopyranoside (122588-57-2) → (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran (122588-56-1) + methyl 2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside (122588-59-4)

Guidance literature:

methyl-2,3,4,6-tetra-O-benzyl-7-(dimethylphenyl-silyl)-L-glycero-α-Dmanno-heptopyranoside; With potassium acetate; acetic acid; potassium bromide; at 6.9 ℃; for 0.25h; Inert atmosphere;

With peracetic acid; at 6.9 - 22.4 ℃; for 5h; Inert atmosphere;

DOI:10.1016/j.carres.2016.07.010

upstream raw materials:

methyl-2,3,4-tri-O-benzyl-7-(Si-dimethylphenyl-silyl)-L-glycero-α-Dmanno-heptopyranoside

methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside

Methyltriphenylphosphonium bromide

methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

C₅₆H₆₀O₁₀

6-(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-manno-pyranozide) boronic acid

methyl-2,3,4-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside

methyl 2,3,4-tri-O-benzyl-D-glycero-α-D-manno-heptopyranoside