phenyl 3-O-benzyl-6-deoxy-4-O-methyl-2-O-phenoxythionocarbonyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 3-O-benzyl-6-deoxy-4-O-methyl-2-O-phenoxythionocarbonyl-1-thio-β-D-glucopyranoside
• CAS No.: 176039-97-7
• Molecular Formula: C₂₇H₂₈O₅S₂
• Molecular Weight: 496.648

Synonyms:phenyl 3-O-benzyl-6-deoxy-4-O-methyl-2-O-phenoxythionocarbonyl-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 3-O-benzyl-6-deoxy-4-O-methyl-2-O-phenoxythionocarbonyl-1-thio-β-D-glucopyranoside

Chemical Property:

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Technology Process of phenyl 3-O-benzyl-6-deoxy-4-O-methyl-2-O-phenoxythionocarbonyl-1-thio-β-D-glucopyranoside

There total 6 articles about phenyl 3-O-benzyl-6-deoxy-4-O-methyl-2-O-phenoxythionocarbonyl-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: 77.0%

phenyl 3-O-benzyl-6-deoxy-4-O-methyl-1-thio-β-D-glucopyranoside (176039-96-6) + phenylcarbonochloridothioate (1005-56-7) → phenyl 3-O-benzyl-6-deoxy-4-O-methyl-2-O-phenoxythionocarbonyl-1-thio-β-D-glucopyranoside (176039-97-7)

Guidance literature:

With dmap; In acetonitrile; for 24h; Ambient temperature;

DOI:10.1016/0040-4020(96)00035-X

Reference yield:

benzyl bromide (100-39-0) → phenyl 3-O-benzyl-6-deoxy-4-O-methyl-2-O-phenoxythionocarbonyl-1-thio-β-D-glucopyranoside (176039-97-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) dibutyltin oxide, 2.) cesium fluoride / 1.) methanol, reflux, 2 h, 2.) DMF, RT, 17 h

2: 79 percent / NaH / dimethylformamide / 2 h / Ambient temperature

3: 3,3-dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / 0 °C

4: 1.) potassium carbonate, 18-crown-6 / 1.) acetone, reflux, 2 h, 2.) acetone, RT, 30 min

5: 77 percent / DMAP / acetonitrile / 24 h / Ambient temperature

With dmap; 18-crown-6 ether; 3,3-dimethyldioxirane; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; cesium fluoride; In dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/0040-4020(96)00035-X

Reference yield:

(2R,3S,4R)-2-Methyl-3,4-dihydro-2H-pyran-3,4-diol (78086-61-0) → phenyl 3-O-benzyl-6-deoxy-4-O-methyl-2-O-phenoxythionocarbonyl-1-thio-β-D-glucopyranoside (176039-97-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) dibutyltin oxide, 2.) cesium fluoride / 1.) methanol, reflux, 2 h, 2.) DMF, RT, 17 h

2: 79 percent / NaH / dimethylformamide / 2 h / Ambient temperature

3: 3,3-dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / 0 °C

4: 1.) potassium carbonate, 18-crown-6 / 1.) acetone, reflux, 2 h, 2.) acetone, RT, 30 min

5: 77 percent / DMAP / acetonitrile / 24 h / Ambient temperature

With dmap; 18-crown-6 ether; 3,3-dimethyldioxirane; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; cesium fluoride; In dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/0040-4020(96)00035-X

upstream raw materials:

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

phenylcarbonochloridothioate

benzyl bromide

(2R,3S,4R)-2-Methyl-3,4-dihydro-2H-pyran-3,4-diol

Downstream raw materials:

4-[2-(benzylcarbonylamino)ethyl]phenyl 2,4-di-O-methyl-3-O-{4-O-benzyl-2-O-methyl-3-O-[4-O-acetyl-2-O-methyl-3-O-(3-O-benzyl-2,6-dideoxy-4-O-methyl-α-D-arabino-hexopyranosyl)-α-L-fucopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside

4-[2-(benzylcarbonylamino)ethyl]phenyl 2,4-di-O-methyl-3-O-{4-O-benzyl-2-O-methyl-3-O-[4-O-acetyl-2-O-methyl-3-O-(3-O-benzyl-2,6-dideoxy-4-O-methyl-2-phenylthio-α-D-arabino-hexopyranosyl)-α-L-fucopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside

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