phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside
CAS No.:316188-14-4
Molecular Formula:C₂₉H₃₂O₅S
Molecular Weight:492.636
Hs Code.:

Synonyms:phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

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Technology Process of phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

There total 5 articles about phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-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: 94.0%

: 100-39-0
benzyl bromide

: 126092-08-8
phenyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

: 316188-14-4
phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2012.06.061

Reference yield:

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

: 316188-14-4
phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / 1H-imidazole / dimethylformamide / 24 h / 20 °C

2: 86 percent / TsOH / 24 h / 20 °C

3: 89 percent / Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

4: 85 percent / NaH / dimethylformamide / 1 h / 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Substitution / 2: acetalization / 3: ether cleavage / 4: Alkylation;
DOI:10.1002/1522-2675(20001004)83:10<2655::AID-HLCA2655>3.0.CO;2-U

Reference yield:

: 310870-40-7
phenyl 6-O-[(tert-butyl)diphenylsilyl]-1-thio-α-D-mannopyranoside

: 316188-14-4
phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / TsOH / 24 h / 20 °C

2: 89 percent / Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

3: 85 percent / NaH / dimethylformamide / 1 h / 20 °C

With tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide; 1: acetalization / 2: ether cleavage / 3: Alkylation;
DOI:10.1002/1522-2675(20001004)83:10<2655::AID-HLCA2655>3.0.CO;2-U