phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(naphth-2-ylmethyl)-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(naphth-2-ylmethyl)-1-thio-α-D-mannopyranoside
• CAS No.: 1262233-42-0
• Molecular Formula: C₃₇H₃₄O₅S
• Molecular Weight: 590.74

Synonyms:phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(naphth-2-ylmethyl)-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(naphth-2-ylmethyl)-1-thio-α-D-mannopyranoside

Chemical Property:

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Technology Process of phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(naphth-2-ylmethyl)-1-thio-α-D-mannopyranoside

There total 2 articles about phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(naphth-2-ylmethyl)-1-thio-α-D-mannopyranoside 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: 98.0%

2-bromomethylnaphthyl bromide (939-26-4) + phenyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside (158716-08-6) → phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(naphth-2-ylmethyl)-1-thio-α-D-mannopyranoside (1262233-42-0)

Guidance literature:

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

DOI:10.1002/anie.201902507

Reference yield: 95.0%

phenyl 4,6-O-benzylidene-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside (951025-06-2) + benzyl bromide (100-39-0) → phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(naphth-2-ylmethyl)-1-thio-α-D-mannopyranoside (1262233-42-0)

Guidance literature:

phenyl 4,6-O-benzylidene-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃;

DOI:10.1002/chem.201001295

Reference yield: 88.0%

phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(naphth-2-ylmethyl)-1-thio-α-D-mannopyranoside (1262233-42-0) → phenyl 2-O-benzyl-3-O-(naphth-2-ylmethyl)-1-thio-α-D-mannopyranoside

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 5h;

DOI:10.1002/anie.201902507

upstream raw materials:

phenyl 4,6-O-benzylidene-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside

benzyl bromide

2-bromomethylnaphthyl bromide

phenyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside

Downstream raw materials:

S-phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside S-oxide

methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside

methyl 2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside

methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranosyl-(1->4)-2,3-O-isopropylidene-β-D-xylopyranoside

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