(+)-(1S,3R,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-<(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-endo-ol

Base Information

Chemical Name:(+)-(1S,3R,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-<(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-endo-ol
CAS No.:134160-53-5
Molecular Formula:C₂₇H₃₃ClO₁₁Se
Molecular Weight:647.965
Hs Code.:

Synonyms:(+)-(1S,3R,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-<(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-endo-ol

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Chemical Property of (+)-(1S,3R,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-<(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-endo-ol

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Technology Process of (+)-(1S,3R,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-<(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-endo-ol

There total 3 articles about (+)-(1S,3R,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-<(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-endo-ol 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: 99.7%

: 134160-52-4
(+)-(1S,3R,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-<(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-one

: 134160-53-5
(+)-(1S,3R,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-<(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-endo-ol

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; for 0.166667h;
DOI:10.1021/jo00033a032

Reference yield:

: 134160-51-3
(-)-(1S,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7-oxabicyclo<2.2.1>heptan-2-one

: 134160-53-5
(+)-(1S,3R,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-<(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-endo-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 48.5 percent / Bu₃SnH, AIBN / benzene / 1 h / Heating

2: 96 percent / NaBH₄ / methanol; tetrahydrofuran / 0.17 h / 0 °C

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; methanol; benzene;
DOI:10.1016/0040-4039(91)80349-B

Reference yield:

: 128530-72-3
(-)-(1S,4R,5R,6R)-5-exo-benzeneselenyl-2-<(tert-butyl)dimethylsilyloxy>-6-endo-chloro-7-oxabicyclo<2.2.1>hept-2-ene

: 134160-53-5
(+)-(1S,3R,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-<(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-endo-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / HMPT / tetrahydrofuran / 24 h / Heating

2: 48.5 percent / Bu₃SnH, AIBN / benzene / 1 h / Heating

3: 96 percent / NaBH₄ / methanol; tetrahydrofuran / 0.17 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; methanol; benzene;
DOI:10.1016/0040-4039(91)80349-B