phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside
• CAS No.: 158716-10-0
• Molecular Formula: C₂₈H₂₈O₆S
• Molecular Weight: 492.593

Synonyms:phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside

There total 9 articles about phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-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%

acetic anhydride (108-24-7) + phenyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside (158716-08-6) → phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside (158716-10-0)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/jo902254w

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside (158716-10-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 69 percent / tetrafluoroboric acid / diethyl ether; dimethylformamide / 3 h / 20 °C

2.1: dibutyltin oxide / toluene / 4 h / Heating

2.2: 81 percent / tetrabutylammonium iodide / toluene / 5 h / Heating

3.1: 90 percent / NaH; tetrabutylammonium iodide / dimethylformamide / 48 h / 20 °C

4.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 24 h / 20 °C

5.1: 92 percent / pyridine / 5 h / 20 °C

With tetrafluoroboric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In pyridine; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Etherification / 2.1: Addition / 2.2: Alkylation / 3.1: Alkylation / 4.1: Hydrolysis / 5.1: Acetylation;

DOI:10.1080/07328309808001894

Reference yield:

(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-63-1,105088-17-3,149495-84-1,77481-62-0) → phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside (158716-10-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 69 percent / tetrafluoroboric acid / diethyl ether; dimethylformamide / 3 h / 20 °C

2.1: dibutyltin oxide / toluene / 4 h / Heating

2.2: 81 percent / tetrabutylammonium iodide / toluene / 5 h / Heating

3.1: 90 percent / NaH; tetrabutylammonium iodide / dimethylformamide / 48 h / 20 °C

4.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 24 h / 20 °C

5.1: 92 percent / pyridine / 5 h / 20 °C

With tetrafluoroboric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In pyridine; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Etherification / 2.1: Addition / 2.2: Alkylation / 3.1: Alkylation / 4.1: Hydrolysis / 5.1: Acetylation;

DOI:10.1080/07328309808001894

upstream raw materials:

acetic anhydride

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

benzaldehyde dimethyl acetal

(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

Downstream raw materials:

methyl (3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl)-(1-2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

methyl (2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl)-(1-2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-3)-(2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl)-(1-2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

6'-azidohexyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

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