3,6-anhydro-7-O-benzyl-1,2-dideoxy-4,5-O-isopropylidene-2-Se-2-seleno-D-glycero-D-manno-heptitol

Base Information

Chemical Name:3,6-anhydro-7-O-benzyl-1,2-dideoxy-4,5-O-isopropylidene-2-Se-2-seleno-D-glycero-D-manno-heptitol
CAS No.:115936-44-2
Molecular Formula:C₂₃H₂₈O₄Se
Molecular Weight:447.433
Hs Code.:

Synonyms:3,6-anhydro-7-O-benzyl-1,2-dideoxy-4,5-O-isopropylidene-2-Se-2-seleno-D-glycero-D-manno-heptitol

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Chemical Property of 3,6-anhydro-7-O-benzyl-1,2-dideoxy-4,5-O-isopropylidene-2-Se-2-seleno-D-glycero-D-manno-heptitol

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Technology Process of 3,6-anhydro-7-O-benzyl-1,2-dideoxy-4,5-O-isopropylidene-2-Se-2-seleno-D-glycero-D-manno-heptitol

There total 8 articles about 3,6-anhydro-7-O-benzyl-1,2-dideoxy-4,5-O-isopropylidene-2-Se-2-seleno-D-glycero-D-manno-heptitol 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: 8.0%

: 5707-04-0
Phenylselenyl chloride

: 115889-74-2
(E)-7-O-benzyl-1,2,3-trideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol

: 115936-44-2
3,6-anhydro-7-O-benzyl-1,2-dideoxy-4,5-O-isopropylidene-2-Se-2-seleno-D-glycero-D-manno-heptitol

: 115936-43-1
3,6-anhydro-7-O-benzyl-1,2-dideoxy-4,5-O-isopropylidene-2-Se-phenyl-2-seleno-D-glycero-D-allo-heptitol

Guidance literature:: With potassium carbonate; In tetrahydrofuran; at -78 - 25 ℃; Title compound not separated from byproducts;
DOI:10.1021/jo00263a017

Reference yield:

: 198969-39-0
5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose

: 115936-44-2
3,6-anhydro-7-O-benzyl-1,2-dideoxy-4,5-O-isopropylidene-2-Se-2-seleno-D-glycero-D-manno-heptitol

Guidance literature:: Multi-step reaction with 8 steps

1: 80 percent / CH₂Cl₂ / 4 h / Heating

2: 85 percent / 2,6-dimethylpyridine / CH₂Cl₂ / 0.5 h / 25 °C

3: 60 percent / ethanethiol, n-BuLi / tetrahydrofuran / 1.5 h / 25 °C

4: 89 percent / DIBAL / diethyl ether / 1 h / 0 °C

5: 58 percent / methanesulfonyl chloride, 2,4,6-trimethylpyridine, lithium chloride / N,N-dimethyl-acetamide / 2 h / 0 °C

6: 90 percent / LiBEt₃H / tetrahydrofuran / 6 h / 25 °C

7: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 25 °C

8: 44 percent / K₂CO₃ / tetrahydrofuran / -78 - 25 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; n-butyllithium; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; lithium triethylborohydride; potassium carbonate; methanesulfonyl chloride; ethanethiol; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl acetamide;
DOI:10.1021/jo00263a017

Reference yield:

: 115857-82-4
(E)-7-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2,3-trideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol

: 115936-44-2
3,6-anhydro-7-O-benzyl-1,2-dideoxy-4,5-O-isopropylidene-2-Se-2-seleno-D-glycero-D-manno-heptitol

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 25 °C

2: 44 percent / K₂CO₃ / tetrahydrofuran / -78 - 25 °C

With tetrabutyl ammonium fluoride; potassium carbonate; In tetrahydrofuran;
DOI:10.1021/jo00263a017