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

Base Information

Chemical Name:benzyl 7-O-tetra-butyldiphenylsilyl-2,3,4-O-tri-benzyl-6-deoxy-glycero-α-D-mannoheptopyranoside
CAS No.:1554005-00-3
Molecular Formula:C₅₁H₅₆O₆Si
Molecular Weight:793.088
Hs Code.:

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

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

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

There total 11 articles about benzyl 7-O-tetra-butyldiphenylsilyl-2,3,4-O-tri-benzyl-6-deoxy-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: 63.0%

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

: 1554005-00-3
benzyl 7-O-tetra-butyldiphenylsilyl-2,3,4-O-tri-benzyl-6-deoxy-glycero-α-D-mannoheptopyranoside

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In hexane; toluene; at 60 ℃; for 4h; 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

: 1554005-00-3
benzyl 7-O-tetra-butyldiphenylsilyl-2,3,4-O-tri-benzyl-6-deoxy-glycero-α-D-mannoheptopyranoside

Guidance literature:: Multi-step reaction with 5 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

5.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / hexane; toluene / 4 h / 60 °C / Inert atmosphere

With 1H-imidazole; dmap; osmium(VIII) oxide; n-butyllithium; 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination;
DOI:10.1016/j.bmc.2013.12.019

Reference yield:

: 530-26-7
D-Mannose

: 1554005-00-3
benzyl 7-O-tetra-butyldiphenylsilyl-2,3,4-O-tri-benzyl-6-deoxy-glycero-α-D-mannoheptopyranoside

Guidance literature:: Multi-step reaction with 10 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

10.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / hexane; toluene / 4 h / 60 °C / Inert atmosphere

With 1H-imidazole; dmap; osmium(VIII) oxide; n-butyllithium; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; sodium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; acetyl chloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil; 5.1: |Dess-Martin Oxidation / 6.1: |Wittig Olefination / 6.2: |Wittig Olefination;
DOI:10.1016/j.bmc.2013.12.019