benzyl 7-O-tetra-butyldiphenylsilyl-6-O-(phenorythiocarbonyl)-2,3,4-O-tri-benzyl-D-glycero-α-D-mannoheptopyranoside

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Chemical Name:benzyl 7-O-tetra-butyldiphenylsilyl-6-O-(phenorythiocarbonyl)-2,3,4-O-tri-benzyl-D-glycero-α-D-mannoheptopyranoside
CAS No.:1554004-98-6
Molecular Formula:C₅₈H₆₀O₈SSi
Molecular Weight:945.261
Hs Code.:

Synonyms:benzyl 7-O-tetra-butyldiphenylsilyl-6-O-(phenorythiocarbonyl)-2,3,4-O-tri-benzyl-D-glycero-α-D-mannoheptopyranoside

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Chemical Property of benzyl 7-O-tetra-butyldiphenylsilyl-6-O-(phenorythiocarbonyl)-2,3,4-O-tri-benzyl-D-glycero-α-D-mannoheptopyranoside

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Technology Process of benzyl 7-O-tetra-butyldiphenylsilyl-6-O-(phenorythiocarbonyl)-2,3,4-O-tri-benzyl-D-glycero-α-D-mannoheptopyranoside

There total 10 articles about benzyl 7-O-tetra-butyldiphenylsilyl-6-O-(phenorythiocarbonyl)-2,3,4-O-tri-benzyl-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: 72.0%

: 1554004-75-9
benzyl 7-O-tetra-butyldiphenylsilyl-2,3,4-O-tri-benzyl-D-glycero-α-D-mannoheptopyranoside

: 1005-56-7
phenylcarbonochloridothioate

: 1554004-98-6
benzyl 7-O-tetra-butyldiphenylsilyl-6-O-(phenorythiocarbonyl)-2,3,4-O-tri-benzyl-D-glycero-α-D-mannoheptopyranoside

Guidance literature:: With dmap; In acetonitrile; at 60 ℃; for 5h; Inert atmosphere;
DOI:10.1016/j.bmc.2013.12.019

Reference yield:

: 102046-36-6
(2S,3S,4S,5S,6S)-3,4,5,6-tetrabenzyloxytetrahydropyran-2-carbaldehyde

: 1554004-98-6
benzyl 7-O-tetra-butyldiphenylsilyl-6-O-(phenorythiocarbonyl)-2,3,4-O-tri-benzyl-D-glycero-α-D-mannoheptopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -40 °C / Inert atmosphere

1.2: 5 h / -40 - 20 °C

2.1: water; 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone / 4 h / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 0 - 20 °C

4.1: dmap / acetonitrile / 5 h / 60 °C / Inert atmosphere

With 1H-imidazole; dmap; osmium(VIII) oxide; n-butyllithium; water; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetone; acetonitrile; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination;
DOI:10.1016/j.bmc.2013.12.019

Reference yield:

: 530-26-7
D-Mannose

: 1554004-98-6
benzyl 7-O-tetra-butyldiphenylsilyl-6-O-(phenorythiocarbonyl)-2,3,4-O-tri-benzyl-D-glycero-α-D-mannoheptopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1.1: acetyl chloride / 2 h / 50 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 0 - 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

5.1: Dess-Martin periodane / dichloromethane / 0.67 h / 20 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -40 °C / Inert atmosphere

6.2: 5 h / -40 - 20 °C

7.1: water; 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone / 4 h / 20 °C

8.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 0 - 20 °C

9.1: dmap / acetonitrile / 5 h / 60 °C / Inert atmosphere

With 1H-imidazole; dmap; osmium(VIII) oxide; n-butyllithium; tetrabutyl ammonium fluoride; water; sodium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; acetyl chloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; mineral oil; 5.1: |Dess-Martin Oxidation / 6.1: |Wittig Olefination / 6.2: |Wittig Olefination;
DOI:10.1016/j.bmc.2013.12.019