rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(m-iodo-p-methoxyphenyl)-5-(methoxymethoxy)-4,6-dimethyl-2H-pyran-3,4-diol

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Chemical Name:rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(m-iodo-p-methoxyphenyl)-5-(methoxymethoxy)-4,6-dimethyl-2H-pyran-3,4-diol
CAS No.:143191-48-4
Molecular Formula:C₁₆H₂₃IO₆
Molecular Weight:438.26
Hs Code.:

Synonyms:rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(m-iodo-p-methoxyphenyl)-5-(methoxymethoxy)-4,6-dimethyl-2H-pyran-3,4-diol

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Chemical Property of rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(m-iodo-p-methoxyphenyl)-5-(methoxymethoxy)-4,6-dimethyl-2H-pyran-3,4-diol

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Technology Process of rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(m-iodo-p-methoxyphenyl)-5-(methoxymethoxy)-4,6-dimethyl-2H-pyran-3,4-diol

There total 9 articles about rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(m-iodo-p-methoxyphenyl)-5-(methoxymethoxy)-4,6-dimethyl-2H-pyran-3,4-diol 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: 93.0%

: 143191-47-3
rel-(2R,3R,6R)-3,6-dihydro-6-(m-iodo-p-methoxyphenyl)-3-(methoxymethoxy)-2,4-dimethyl-2H-pyran

: 143191-48-4
rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(m-iodo-p-methoxyphenyl)-5-(methoxymethoxy)-4,6-dimethyl-2H-pyran-3,4-diol

Guidance literature:: With 4-methylmorpholine N-oxide; osmium(VIII) oxide; In water; acetone; for 80h;
DOI:10.1021/jo00047a020

Reference yield:

: 83569-29-3
cis,cis-2-methyl-3-hydroxy-4-(iodomethyl)-γ-butyrolactone

: 143191-48-4
rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(m-iodo-p-methoxyphenyl)-5-(methoxymethoxy)-4,6-dimethyl-2H-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / n-Bu₃SnH, AIBN / a) benzene, reflux, 6 h, b) benzene, CCl₄, 12 h

2: 94 percent / diisopropylethylamine / CH₂Cl₂ / 72 h / Ambient temperature

3: 81 percent / diisobutylaluminum hydride / toluene / 0.17 h / -78 °C

4: 1) lithium diisopropylamide / 1) THF, -75 deg C, 45 min, 2) THF, a) -80 deg C, 30 min, b) to room temperature

5: 75 percent / CH₂Cl₂ / 1.5 h / -78 °C

6: 69 percent / 30percent aq. H₂O₂, pyridine / tetrahydrofuran / a) 0 deg C, 30 min, b) to room temperature, 8 h

7: 93 percent / N-methylmorpholine N-oxide / OsO₄ / acetone; H₂O / 80 h

With pyridine; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; acetone; toluene;
DOI:10.1021/jo00047a020

Reference yield:

: 143191-43-9
3-iodo-4-methoxybenzyl chloride

: 143191-48-4
rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(m-iodo-p-methoxyphenyl)-5-(methoxymethoxy)-4,6-dimethyl-2H-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / 8 h / 160 °C

2: 1) lithium diisopropylamide / 1) THF, -75 deg C, 45 min, 2) THF, a) -80 deg C, 30 min, b) to room temperature

3: 75 percent / CH₂Cl₂ / 1.5 h / -78 °C

4: 69 percent / 30percent aq. H₂O₂, pyridine / tetrahydrofuran / a) 0 deg C, 30 min, b) to room temperature, 8 h

5: 93 percent / N-methylmorpholine N-oxide / OsO₄ / acetone; H₂O / 80 h

With pyridine; dihydrogen peroxide; 4-methylmorpholine N-oxide; lithium diisopropyl amide; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; acetone;
DOI:10.1021/jo00047a020