methyl 2,3,4-tri-O-benzyl-5-methylene-α-D-lyxopyranoside

Base Information

• Chemical Name: methyl 2,3,4-tri-O-benzyl-5-methylene-α-D-lyxopyranoside
• CAS No.: 155049-46-0
• Molecular Formula: C₂₈H₃₀O₅
• Molecular Weight: 446.543

Synonyms:methyl 2,3,4-tri-O-benzyl-5-methylene-α-D-lyxopyranoside

Chemical Property of methyl 2,3,4-tri-O-benzyl-5-methylene-α-D-lyxopyranoside

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Technology Process of methyl 2,3,4-tri-O-benzyl-5-methylene-α-D-lyxopyranoside

There total 15 articles about methyl 2,3,4-tri-O-benzyl-5-methylene-α-D-lyxopyranoside 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: 86.0%

methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-α-D-manno-pyranoside (291753-79-2) → methyl 2,3,4-tri-O-benzyl-5-methylene-α-D-lyxopyranoside (155049-46-0)

Guidance literature:

With pyridine; silver fluoride; at 20 ℃; for 48h; Inert atmosphere; Darkness;

DOI:10.1021/acs.joc.7b03079

Reference yield: 26.0%

caprolactam (105-60-2,9012-16-2) + methyl 6-deoxy-6-N-piperidine-2-one-α-D-galctopyranoside (1270918-45-0) → methyl 6-deoxy-2,3,4-tri-O-benzyl-6-N-azepan-2-one-α-D-mannopyranoside (1270918-52-9) + methyl 2,3,4-tri-O-benzyl-5-methylene-α-D-lyxopyranoside (155049-46-0)

Guidance literature:

caprolactam; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

methyl 6-deoxy-6-N-piperidine-2-one-α-D-galctopyranoside; In tetrahydrofuran; at 20 - 50 ℃; for 14h; Inert atmosphere;

DOI:10.1039/c0ob00719f

Reference yield:

C21H24O5 (1313193-62-2) + benzyl bromide (100-39-0) → methyl 2,3,4-tri-O-benzyl-5-methylene-α-D-lyxopyranoside (155049-46-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.tet.2011.04.082

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-α-D-manno-pyranoside

benzyl bromide

methyl 2,3,4-tri-O-trimethylsilyl-5-methylene-α-D-lyxopyranoside

methyl 6-deoxy-6-iodo-α-D-mannopyrannoside

Downstream raw materials:

(3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-one

C₂₇H₂₆O₄

(4R,5R,6S)-4,5,6-tris(benzyloxy)-2-iodocyclohex-2-en-1-one

(4R,5R,6S)-4,5,6-tris(benzyloxy)-2-methylcyclohex-2-enone

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