(+)-(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

Base Information

Chemical Name:(+)-(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
CAS No.:134160-52-4
Molecular Formula:C₂₇H₃₁ClO₁₁Se
Molecular Weight:645.95
Hs Code.:

Synonyms:(+)-(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

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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-α-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-one

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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-α-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-one

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-α-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-one 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: 48.5%

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

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 134235-75-9
(+)-(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-one

: 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

: 13137-69-4
1-deoxy-D-glucose tetraacetate

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 1h; Heating;
DOI:10.1016/0040-4039(91)80349-B

Reference yield: 48.0%

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

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 134235-75-9
(+)-(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-one

: 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

: 13137-69-4
1-deoxy-D-glucose tetraacetate

: 16750-06-4
1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-arabinohexopyranose

Guidance literature:: With azobisisobutyronitrile; tri-n-butyl-tin hydride; In toluene; for 1h; Heating;
DOI:10.1021/jo00033a032

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

: 134160-52-4
(+)-(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

Guidance literature:: Multi-step reaction with 2 steps

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

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

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