(2'S,3'S,3R,4R,5S,6R)-1-iodo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-fluoro-cyclohex-1-ene-3,4,5-triol

Base Information

Chemical Name:(2'S,3'S,3R,4R,5S,6R)-1-iodo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-fluoro-cyclohex-1-ene-3,4,5-triol
CAS No.:701211-80-5
Molecular Formula:C₁₉H₂₄FIO₅
Molecular Weight:478.299
Hs Code.:

Synonyms:(2'S,3'S,3R,4R,5S,6R)-1-iodo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-fluoro-cyclohex-1-ene-3,4,5-triol

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Chemical Property of (2'S,3'S,3R,4R,5S,6R)-1-iodo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-fluoro-cyclohex-1-ene-3,4,5-triol

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Technology Process of (2'S,3'S,3R,4R,5S,6R)-1-iodo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-fluoro-cyclohex-1-ene-3,4,5-triol

There total 6 articles about (2'S,3'S,3R,4R,5S,6R)-1-iodo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-fluoro-cyclohex-1-ene-3,4,5-triol 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:

: 596834-80-9
(2'S,3'S,3R,4R,5S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohex-1-ene-3,4,5,6-tetraol

: 701211-80-5
(2'S,3'S,3R,4R,5S,6R)-1-iodo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-fluoro-cyclohex-1-ene-3,4,5-triol

Guidance literature:: Multi-step reaction with 2 steps

1: potassium iodide / copper(I) iodide; N,N'-dimethylethylenediamine / butan-1-ol / 24 h / 120 °C

2: 0.057 g / Et₂NSF₃ / CH₂Cl₂ / -78 - 20 °C

With diethylamino-sulfur trifluoride; potassium iodide; copper(l) iodide; N,N`-dimethylethylenediamine; In dichloromethane; butan-1-ol;
DOI:10.1016/j.tet.2006.03.029

Reference yield:

: 138769-92-3
cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene

: 701211-80-5
(2'S,3'S,3R,4R,5S,6R)-1-iodo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-fluoro-cyclohex-1-ene-3,4,5-triol

Guidance literature:: Multi-step reaction with 6 steps

1.1: p-TSA / CH₂Cl₂ / 1 h / 20 °C

2.1: 1.175 g / N-methylmorpholine N-oxide; water / OsO₄ / 2-methyl-propan-2-ol / 36 h / 20 °C

3.1: Bu₂SnO / methanol; toluene / 3 h / 130 °C

3.2: 91 percent / Bu₄NBr / toluene / 6 h / 130 °C

4.1: 100 percent / TFA; water / 3 h / 20 °C

5.1: CSA / methanol / 24 h / Heating

6.1: 0.057 g / Et₂NSF₃ / CH₂Cl₂ / -78 - 20 °C

With diethylamino-sulfur trifluoride; camphor-10-sulfonic acid; water; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; trifluoroacetic acid; osmium(VIII) oxide; toluene-4-sulfonic acid; In methanol; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1016/j.tet.2006.03.029

Reference yield:

: 154784-39-1
(3aS,7aS)-4-iodo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole

: 701211-80-5
(2'S,3'S,3R,4R,5S,6R)-1-iodo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-fluoro-cyclohex-1-ene-3,4,5-triol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1.175 g / N-methylmorpholine N-oxide; water / OsO₄ / 2-methyl-propan-2-ol / 36 h / 20 °C

2.1: Bu₂SnO / methanol; toluene / 3 h / 130 °C

2.2: 91 percent / Bu₄NBr / toluene / 6 h / 130 °C

3.1: 100 percent / TFA; water / 3 h / 20 °C

4.1: CSA / methanol / 24 h / Heating

5.1: 0.057 g / Et₂NSF₃ / CH₂Cl₂ / -78 - 20 °C

With diethylamino-sulfur trifluoride; camphor-10-sulfonic acid; water; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; trifluoroacetic acid; osmium(VIII) oxide; In methanol; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1016/j.tet.2006.03.029