phenyl 2,3,4-tri-O-benzyl-7-O-triisopropylsilyl-1-thio-D-glycero-α-D-mannoheptopyranoside

Base Information

Chemical Name:phenyl 2,3,4-tri-O-benzyl-7-O-triisopropylsilyl-1-thio-D-glycero-α-D-mannoheptopyranoside
CAS No.:1378358-06-5
Molecular Formula:C₄₃H₅₆O₆SSi
Molecular Weight:729.066
Hs Code.:

Synonyms:phenyl 2,3,4-tri-O-benzyl-7-O-triisopropylsilyl-1-thio-D-glycero-α-D-mannoheptopyranoside

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Chemical Property of phenyl 2,3,4-tri-O-benzyl-7-O-triisopropylsilyl-1-thio-D-glycero-α-D-mannoheptopyranoside

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Technology Process of phenyl 2,3,4-tri-O-benzyl-7-O-triisopropylsilyl-1-thio-D-glycero-α-D-mannoheptopyranoside

There total 9 articles about phenyl 2,3,4-tri-O-benzyl-7-O-triisopropylsilyl-1-thio-D-glycero-α-D-mannoheptopyranoside 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:

: 13154-24-0
triisopropylsilyl chloride

: 1345664-75-6
phenyl 1-deoxy-2,3,4-tri-O-benzyl-1-thio-D-glycero-α-D-manno-heptopyranoside

: 1378358-06-5
phenyl 2,3,4-tri-O-benzyl-7-O-triisopropylsilyl-1-thio-D-glycero-α-D-mannoheptopyranoside

Guidance literature:: With 1H-imidazole; In tetrahydrofuran; at 0 - 20 ℃; for 16h; Inert atmosphere;
DOI:10.1002/chem.201100396

Reference yield:

: 13154-24-0
triisopropylsilyl chloride

: 2,3,4-tri-O-benzyl-1-thioglycero-α-D-mannoheptopyranoside

: 1378358-06-5
phenyl 2,3,4-tri-O-benzyl-7-O-triisopropylsilyl-1-thio-D-glycero-α-D-mannoheptopyranoside

: phenyl 2,3,4-tri-O-benzyl-7-O-triisopropylsilyl-1-thio-L-glycero-α-D-mannoheptopyranoside

Guidance literature:: With 1H-imidazole; dmap; In tetrahydrofuran; at 0 - 20 ℃; for 16h; Overall yield = 74 %; Overall yield = 3.904 g; Inert atmosphere;
DOI:10.1002/ejoc.201301071

Reference yield:

: 1378357-82-4
phenyl 2,3,4-tri-O-benzyl-α-D-mannohexodialdopyranoside

: 1378358-06-5
phenyl 2,3,4-tri-O-benzyl-7-O-triisopropylsilyl-1-thio-D-glycero-α-D-mannoheptopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 20 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: potassium osmate(VI) dihydrate; water; potassium carbonate; potassium hexacyanoferrate(III) / toluene; tert-butyl alcohol / 96 h / 0 - 20 °C / Inert atmosphere

3.1: 1H-imidazole / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; potassium osmate(VI) dihydrate; n-butyllithium; water; potassium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; hexane; toluene; tert-butyl alcohol; 1.1: Wittig olefinization / 1.2: Wittig olefinization;
DOI:10.1002/chem.201100396