rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(p-methoxyphenyl)-4,6-dimethyl-2H-pyran-3,4,5-triol

Base Information

Chemical Name:rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(p-methoxyphenyl)-4,6-dimethyl-2H-pyran-3,4,5-triol
CAS No.:143191-42-8
Molecular Formula:C₁₄H₂₀O₅
Molecular Weight:268.31
Hs Code.:

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

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

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

There total 9 articles about rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(p-methoxyphenyl)-4,6-dimethyl-2H-pyran-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: 69.0%

: 143191-41-7
rel-(2S,3S,4S,5S,6R)-tetrahydro-5-(methoxymethoxy)-2-(p-methoxyphenyl)-4,6-dimethyl-2H-pyran-3,4-diol

: 143191-42-8
rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(p-methoxyphenyl)-4,6-dimethyl-2H-pyran-3,4,5-triol

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; for 2h; Heating;
DOI:10.1021/jo00047a020

Reference yield:

: 1145-93-3
diethyl 4-methoxybenzylphosphonate

: 143191-42-8
rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(p-methoxyphenyl)-4,6-dimethyl-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 5 steps

1: 1) a) n-BuLi, 2) NaH / 1) DME, a) -78 deg C, 1 h, b) to room temperature, 30 min, 2) benzene, reflux, 30 min

2: 74 percent / CH₂Cl₂ / 0.5 h / -78 °C

3: 79 percent / H₂O₂, pyridine / tetrahydrofuran / a) 0 deg C, 30 min, b) to room temperature, 8 h

4: 88 percent / N-methylmorpholine N-oxide, / OsO₄ / acetone; H₂O / 48 h

5: 69 percent / 2 N aq. HCl / tetrahydrofuran / 2 h / Heating

With pyridine; hydrogenchloride; n-butyllithium; dihydrogen peroxide; sodium hydride; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; acetone;
DOI:10.1021/jo00047a020

Reference yield:

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

: 143191-42-8
rel-(2S,3S,4S,5S,6R)-tetrahydro-2-(p-methoxyphenyl)-4,6-dimethyl-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 8 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) a) n-BuLi, 2) NaH / 1) DME, a) -78 deg C, 1 h, b) to room temperature, 30 min, 2) benzene, reflux, 30 min

5: 74 percent / CH₂Cl₂ / 0.5 h / -78 °C

6: 79 percent / H₂O₂, pyridine / tetrahydrofuran / a) 0 deg C, 30 min, b) to room temperature, 8 h

7: 88 percent / N-methylmorpholine N-oxide, / OsO₄ / acetone; H₂O / 48 h

8: 69 percent / 2 N aq. HCl / tetrahydrofuran / 2 h / Heating

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