4,5-anhydro-2,3-dideoxy-3-C-methyl-D-erythro-pentitol

Base Information

Chemical Name:4,5-anhydro-2,3-dideoxy-3-C-methyl-D-erythro-pentitol
CAS No.:103233-16-5
Molecular Formula:C₂₅H₂₆O₂
Molecular Weight:358.48
Hs Code.:

Synonyms:

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Chemical Property of 4,5-anhydro-2,3-dideoxy-3-C-methyl-D-erythro-pentitol

Chemical Property:

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Technology Process of 4,5-anhydro-2,3-dideoxy-3-C-methyl-D-erythro-pentitol

There total 30 articles about 4,5-anhydro-2,3-dideoxy-3-C-methyl-D-erythro-pentitol 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: 71.0%

: 120438-32-6
Methanesulfonic acid (1S,2S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-4-trityloxy-butyl ester

: 103233-16-5,103303-18-0
4,5-anhydro-2,3-dideoxy-3-C-methyl-1-O-triphenylmethyl-D-threo-pentitol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Ambient temperature;
DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 103233-16-5,103303-18-0
4,5-anhydro-2,3-dideoxy-3-C-methyl-1-O-triphenylmethyl-D-threo-pentitol

Guidance literature:: Multi-step reaction with 8 steps

1: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

2: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

3: 30percent H₂O₂ / 0 °C

4: 1.) CuBr*Me₂S / 1.) ether, hexane, 0 deg C, 6 min; 2.) -23 deg C, 20 min.

5: 96 percent / borane-dimethylsulphide complex / tetrahydrofuran / 15 h / Ambient temperature

6: pyridine / 4-dimethylaminopyridine / CH₂Cl₂ / 15 h / Ambient temperature

7: DMAP, pyridine / CH₂Cl₂ / 4 h / Ambient temperature

8: 71 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; dmap; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; dihydrogen peroxide; triethylamine; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 103233-16-5,103303-18-0
4,5-anhydro-2,3-dideoxy-3-C-methyl-D-erythro-pentitol

Guidance literature:: Multi-step reaction with 9 steps

1: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

2: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

3: 30percent H₂O₂ / 0 °C

4: 1.) CuBr*Me₂S / 1.) ether, hexane, 0 deg C, 6 min; 2.) -23 deg C, 20 min.

5: 96 percent / borane-dimethylsulphide complex / tetrahydrofuran / 15 h / Ambient temperature

6: pyridine / 4-dimethylaminopyridine / CH₂Cl₂ / 15 h / Ambient temperature

7: 92 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

8: pyridine / 48 h / Ambient temperature

9: sodium methoxide / methanol / 0.25 h / 0 °C

With pyridine; dmap; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; triethylamine; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4020(01)87683-3