(3R,4R,5S,6S)-1-iodo-3-O-benzyl-5-O,6-O-(propane-2,2-diyl)-cyclohex-1-ene-3,4,5,6-tetraol

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Chemical Name:(3R,4R,5S,6S)-1-iodo-3-O-benzyl-5-O,6-O-(propane-2,2-diyl)-cyclohex-1-ene-3,4,5,6-tetraol
CAS No.:485400-33-7
Molecular Formula:C₁₆H₁₉IO₄
Molecular Weight:402.229
Hs Code.:

Synonyms:(3R,4R,5S,6S)-1-iodo-3-O-benzyl-5-O,6-O-(propane-2,2-diyl)-cyclohex-1-ene-3,4,5,6-tetraol

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Chemical Property of (3R,4R,5S,6S)-1-iodo-3-O-benzyl-5-O,6-O-(propane-2,2-diyl)-cyclohex-1-ene-3,4,5,6-tetraol

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Technology Process of (3R,4R,5S,6S)-1-iodo-3-O-benzyl-5-O,6-O-(propane-2,2-diyl)-cyclohex-1-ene-3,4,5,6-tetraol

There total 3 articles about (3R,4R,5S,6S)-1-iodo-3-O-benzyl-5-O,6-O-(propane-2,2-diyl)-cyclohex-1-ene-3,4,5,6-tetraol 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: 91.0%

: 100-39-0
benzyl bromide

: 165611-18-7
(3aS,4R,5R,7aS)-7-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol

: 485400-33-7
(3R,4R,5S,6S)-1-iodo-3-O-benzyl-5-O,6-O-(propane-2,2-diyl)-cyclohex-1-ene-3,4,5,6-tetraol

Guidance literature:: (3aS,4R,5R,7aS)-7-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol; With di(n-butyl)tin oxide; In methanol; toluene; at 130 ℃; for 3h;

benzyl bromide; With tetrabutylammomium bromide; In toluene; at 130 ℃; for 6h;
DOI:10.1016/j.tet.2006.03.029

Reference yield:

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

: 485400-33-7
(3R,4R,5S,6S)-1-iodo-3-O-benzyl-5-O,6-O-(propane-2,2-diyl)-cyclohex-1-ene-3,4,5,6-tetraol

Guidance literature:: Multi-step reaction with 3 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

With water; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; 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

: 485400-33-7
(3R,4R,5S,6S)-1-iodo-3-O-benzyl-5-O,6-O-(propane-2,2-diyl)-cyclohex-1-ene-3,4,5,6-tetraol

Guidance literature:: Multi-step reaction with 2 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

With water; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In methanol; toluene; tert-butyl alcohol;
DOI:10.1016/j.tet.2006.03.029