1,4-dideoxy-1,4-[(2S,3S,4R,5R,6R)-4,6,7-tri-O-benzyl-2,5-O-methylene-3-(sulfooxy)heptyl]-(R)-epi-sulfoniumylidine-D-arabinitol inner salt

Base Information

Chemical Name:1,4-dideoxy-1,4-[(2S,3S,4R,5R,6R)-4,6,7-tri-O-benzyl-2,5-O-methylene-3-(sulfooxy)heptyl]-(R)-epi-sulfoniumylidine-D-arabinitol inner salt
CAS No.:1143516-36-2
Molecular Formula:C₃₄H₄₂O₁₂S₂
Molecular Weight:706.832
Hs Code.:

Synonyms:1,4-dideoxy-1,4-[(2S,3S,4R,5R,6R)-4,6,7-tri-O-benzyl-2,5-O-methylene-3-(sulfooxy)heptyl]-(R)-epi-sulfoniumylidine-D-arabinitol inner salt

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Chemical Property of 1,4-dideoxy-1,4-[(2S,3S,4R,5R,6R)-4,6,7-tri-O-benzyl-2,5-O-methylene-3-(sulfooxy)heptyl]-(R)-epi-sulfoniumylidine-D-arabinitol inner salt

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Technology Process of 1,4-dideoxy-1,4-[(2S,3S,4R,5R,6R)-4,6,7-tri-O-benzyl-2,5-O-methylene-3-(sulfooxy)heptyl]-(R)-epi-sulfoniumylidine-D-arabinitol inner salt

There total 15 articles about 1,4-dideoxy-1,4-[(2S,3S,4R,5R,6R)-4,6,7-tri-O-benzyl-2,5-O-methylene-3-(sulfooxy)heptyl]-(R)-epi-sulfoniumylidine-D-arabinitol inner salt 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: 82.0%

: 1143516-35-1
C₅₈H₆₆O₁₅S₂

: 1143516-36-2
1,4-dideoxy-1,4-[(2S,3S,4R,5R,6R)-4,6,7-tri-O-benzyl-2,5-O-methylene-3-(sulfooxy)heptyl]-(R)-epi-sulfoniumylidine-D-arabinitol inner salt

Guidance literature:: With trifluoroacetic acid; In water; at 20 ℃; for 2h;

Reference yield:

: 28224-73-9
1,3:4,6-di-O-benzylidene-D-mannitol

: 1143516-36-2
1,4-dideoxy-1,4-[(2S,3S,4R,5R,6R)-4,6,7-tri-O-benzyl-2,5-O-methylene-3-(sulfooxy)heptyl]-(R)-epi-sulfoniumylidine-D-arabinitol inner salt

Guidance literature:: Multi-step reaction with 14 steps

1.1: sodium hydroxide / water

2.1: methanol; toluene-4-sulfonic acid / 2 h / 70 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 0 °C / Inert atmosphere

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

4.2: 0 - 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 h / 20 °C

6.1: sodium hydrogencarbonate; Dess-Martin periodane / 0.25 h / 20 °C

7.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

7.2: -78 - 20 °C

8.1: AD-mix-β / water; tert-butyl alcohol / 168 h / 0 °C

9.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / Cooling with ice bath

9.2: 0 - 20 °C

10.1: methanol; toluene-4-sulfonic acid / 24 h / 20 °C

11.1: thionyl chloride; triethylamine / dichloromethane / 0.75 h / Cooling with ice bath

12.1: sodium periodate / ruthenium trichloride / tetrachloromethane; water; acetonitrile / 2 h / 20 °C

13.1: potassium carbonate / 1,1,1,3',3',3'-hexafluoro-propanol / 168 h / 75 °C / Sealed tube

14.1: water; trifluoroacetic acid / 2 h / 20 °C

With 1H-imidazole; methanol; sodium hydroxide; sodium periodate; n-butyllithium; thionyl chloride; AD-mix-β; tetrabutyl ammonium fluoride; water; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; 1,1,1,3',3',3'-hexafluoro-propanol; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; tert-butyl alcohol;

Reference yield:

: 1143516-29-3
4,6,7-tri-O-benzyl-2,5-O-methylene-D-glycero-D-manno-heptitol

: 1143516-36-2
1,4-dideoxy-1,4-[(2S,3S,4R,5R,6R)-4,6,7-tri-O-benzyl-2,5-O-methylene-3-(sulfooxy)heptyl]-(R)-epi-sulfoniumylidine-D-arabinitol inner salt

Guidance literature:: Multi-step reaction with 4 steps

1: thionyl chloride; triethylamine / dichloromethane / 0.75 h / Cooling with ice bath

2: sodium periodate / ruthenium trichloride / tetrachloromethane; water; acetonitrile / 2 h / 20 °C

3: potassium carbonate / 1,1,1,3',3',3'-hexafluoro-propanol / 168 h / 75 °C / Sealed tube

4: water; trifluoroacetic acid / 2 h / 20 °C

With sodium periodate; thionyl chloride; water; potassium carbonate; triethylamine; trifluoroacetic acid; ruthenium trichloride; In tetrachloromethane; dichloromethane; 1,1,1,3',3',3'-hexafluoro-propanol; water; acetonitrile;