benzyl 2,3:5,6-di-O-isopentylidene-α-D-mannofuranoside

Base Information

Chemical Name:benzyl 2,3:5,6-di-O-isopentylidene-α-D-mannofuranoside
CAS No.:1393085-98-7
Molecular Formula:C₂₃H₃₄O₆
Molecular Weight:406.519
Hs Code.:

Synonyms:benzyl 2,3:5,6-di-O-isopentylidene-α-D-mannofuranoside

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Chemical Property of benzyl 2,3:5,6-di-O-isopentylidene-α-D-mannofuranoside

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Technology Process of benzyl 2,3:5,6-di-O-isopentylidene-α-D-mannofuranoside

There total 2 articles about benzyl 2,3:5,6-di-O-isopentylidene-α-D-mannofuranoside 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: 70.0%

: 1393085-97-6
2,3:5,6-di-O-isopentylidene-α-D-mannofuranose

: 100-44-7
benzyl chloride

: 1393085-98-7
benzyl 2,3:5,6-di-O-isopentylidene-α-D-mannofuranoside

Guidance literature:: 2,3:5,6-di-O-isopentylidene-α-D-mannofuranose; With sodium hydride; In N,N-dimethyl-formamide; Inert atmosphere; Cooling;

benzyl chloride; In N,N-dimethyl-formamide; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1016/j.tet.2012.06.065

Reference yield:

: 7322-31-8
β-D-mannose

: 96-22-0
pentan-3-one

: 1393085-98-7
benzyl 2,3:5,6-di-O-isopentylidene-α-D-mannofuranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: sulfuric acid / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere; Cooling

2.2: 4 h / 20 °C / Inert atmosphere

With sulfuric acid; sodium hydride; In N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2012.06.065

Reference yield:

: 1393085-98-7
benzyl 2,3:5,6-di-O-isopentylidene-α-D-mannofuranoside

: 204255-06-1
oseltamivir

Guidance literature:: Multi-step reaction with 15 steps

1.1: hydrogenchloride; water / methanol / 4 h / 20 °C

2.1: sodium periodate / ethanol; water; methanol / 3 h / 20 °C

3.1: copper(II) bis(trifluoromethanesulfonate); borane-THF / 2 h / 20 °C / Inert atmosphere

4.1: 1H-imidazole; dmap / dichloromethane / 24 h / 20 °C / Inert atmosphere

5.1: pyridine / dichloromethane / 1 h / -15 °C / Inert atmosphere

6.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C

7.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C

7.2: 4 h / 20 °C

8.1: pyridine / 2 h / 0 - 20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

10.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -78 °C / Inert atmosphere

10.2: 0.75 h / -78 - 20 °C / Inert atmosphere

11.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

11.2: 2 h / 0 °C / Inert atmosphere

12.1: 10% Pd/C; hydrogen / ethanol / 96 h / 20 °C

13.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

14.1: triethylamine / dichloromethane / 0.75 h / 0 °C

15.1: sodium azide / ethanol; water / 8 h / Reflux

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium periodate; sodium azide; borane-THF; oxalyl dichloride; 10% Pd/C; tetrabutyl ammonium fluoride; water; hydrogen; titanium tetrachloride; copper(II) bis(trifluoromethanesulfonate); sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 7.1: |Staudinger Azide Reduction / 7.2: |Staudinger Azide Reduction / 10.1: |Swern Oxidation / 10.2: |Swern Oxidation / 11.1: |Knoevenagel Condensation / 11.2: |Knoevenagel Condensation;
DOI:org/10.1016/j.tetlet.2012.08.143