phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-phenoxythiocarbonyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-phenoxythiocarbonyl-1-thio-β-D-glucopyranoside
• CAS No.: 141810-62-0
• Molecular Formula: C₃₃H₃₀O₆S₂
• Molecular Weight: 586.73

Synonyms:phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-phenoxythiocarbonyl-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-phenoxythiocarbonyl-1-thio-β-D-glucopyranoside

Chemical Property:

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Technology Process of phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-phenoxythiocarbonyl-1-thio-β-D-glucopyranoside

There total 4 articles about phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-phenoxythiocarbonyl-1-thio-β-D-glucopyranoside 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: 82.0%

phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside (128848-51-1) + phenylcarbonochloridothioate (1005-56-7) → phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-phenoxythiocarbonyl-1-thio-β-D-glucopyranoside (141810-62-0)

Guidance literature:

With dmap; In acetonitrile; for 16h;

DOI:10.1016/S0040-4020(01)80165-4

Reference yield:

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (71676-30-7,87508-18-7,138922-03-9,87508-17-6) → phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-phenoxythiocarbonyl-1-thio-β-D-glucopyranoside (141810-62-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) dibutyltin oxide, 2) CsF / 1) MeOH, reflux, then RT, 4 h, 2) DMF, RT, 16 h

2: 82 percent / DMAP / acetonitrile / 16 h

With dmap; di(n-butyl)tin oxide; cesium fluoride; In acetonitrile;

DOI:10.1016/S0040-4020(01)80165-4

Reference yield:

benzyl bromide (100-39-0) → phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-phenoxythiocarbonyl-1-thio-β-D-glucopyranoside (141810-62-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) dibutyltin oxide, 2) CsF / 1) MeOH, reflux, then RT, 4 h, 2) DMF, RT, 16 h

2: 82 percent / DMAP / acetonitrile / 16 h

With dmap; di(n-butyl)tin oxide; cesium fluoride; In acetonitrile;

DOI:10.1016/S0040-4020(01)80165-4

upstream raw materials:

phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

phenylcarbonochloridothioate

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

benzyl bromide

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phenylthio-α-D-mannopyranosyl)-β-D-galactopyranoside

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