(2S,3R,4S,5S)-5-Acetoxy-4--3-hydroxy-2-methyl-6-<(methylthio)methoxy>-2-(1,4-dioxonaphth-3-yl)tetrahydrpyran

Base Information

Chemical Name:(2S,3R,4S,5S)-5-Acetoxy-4--3-hydroxy-2-methyl-6-<(methylthio)methoxy>-2-(1,4-dioxonaphth-3-yl)tetrahydrpyran
CAS No.:137742-99-5
Molecular Formula:C₂₈H₂₉NO₉S
Molecular Weight:555.606
Hs Code.:

(2S,3R,4S,5S)-5-Acetoxy-4-<N-(benzyloxycarbonyl)amino>-3-hydroxy-2-methyl-6-<(methylthio)methoxy>-2-(1,4-dioxonaphth-3-yl)tetrahydrpyran

Synonyms:(2S,3R,4S,5S)-5-Acetoxy-4--3-hydroxy-2-methyl-6-<(methylthio)methoxy>-2-(1,4-dioxonaphth-3-yl)tetrahydrpyran

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Chemical Property of (2S,3R,4S,5S)-5-Acetoxy-4--3-hydroxy-2-methyl-6-<(methylthio)methoxy>-2-(1,4-dioxonaphth-3-yl)tetrahydrpyran

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Technology Process of (2S,3R,4S,5S)-5-Acetoxy-4--3-hydroxy-2-methyl-6-<(methylthio)methoxy>-2-(1,4-dioxonaphth-3-yl)tetrahydrpyran

There total 15 articles about (2S,3R,4S,5S)-5-Acetoxy-4--3-hydroxy-2-methyl-6-<(methylthio)methoxy>-2-(1,4-dioxonaphth-3-yl)tetrahydrpyran 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: 73.0%

: 137742-97-3,137742-98-4
(2S,3R,4S,5S)-5-Acetoxy-4--3-hydroxy-2-methyl-6-<(methylthio)methoxy>-2-(1-hydroxynaphth-3-yl)tetrahydrpyran

: 137742-99-5
(2S,3R,4S,5S)-5-Acetoxy-4--3-hydroxy-2-methyl-6-<(methylthio)methoxy>-2-(1,4-dioxonaphth-3-yl)tetrahydrpyran

Guidance literature:: With salcomine; oxygen; In tetrahydrofuran; for 1h; Ambient temperature;
DOI:10.1021/jo00028a045

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 137742-99-5
(2S,3R,4S,5S)-5-Acetoxy-4--3-hydroxy-2-methyl-6-<(methylthio)methoxy>-2-(1,4-dioxonaphth-3-yl)tetrahydrpyran

Guidance literature:: Multi-step reaction with 10 steps

1: Na₂CO₃ / diethyl ether / 3 h / 5 °C

2: 90 percent / activated MnO₂ / CHCl₃ / 5 h / Heating

3: 88 percent / diethyl ether / 1) -30 deg C, 30 min., 2) 0 deg C, 30 min., 3) r.t., 1 h

4: 90 percent / propane-1,3-dithiol, BF₃*Et₂O / CH₂Cl₂ / 1) -78 deg C, 2 h, 2) -40 deg C, 2 h, 3) 0 deg C, 1 h

5: 75 percent / DBU / CH₂Cl₂ / 0.67 h / 0 °C

6: 85 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

7: 84 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

8: 1) CF₃COOH, 2) Et₃N / 1) CH₂Cl₂, -70 -> -60 deg C, 3 h, 2) -60 -> 0 deg C, 1 h

9: 78 percent / 1) ZnCl₂, 2) Bu₃SnH / 2) Pd(PPh₃)4 / tetrahydrofuran / 1) r.t., 15 min., 2) 30 min

10: 73 percent / salcomine, O₂ / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; 1.3-propanedithiol; dmap; manganese(IV) oxide; salcomine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; oxygen; tri-n-butyl-tin hydride; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform;
DOI:10.1021/jo00028a045

Reference yield:

: 137742-86-0,137742-87-1
3-<(4R,5R)- and (4S,5S)-3-<(2S)-1,2-(Cyclohexylidenedioxy)eth-2-yl>-4-hydroxy-4,5-dihydroisoxazolin-5-yl>-1-naphthaldehyde

: 137742-99-5
(2S,3R,4S,5S)-5-Acetoxy-4--3-hydroxy-2-methyl-6-<(methylthio)methoxy>-2-(1,4-dioxonaphth-3-yl)tetrahydrpyran

Guidance literature:: Multi-step reaction with 14 steps

1: m-CPBA / CH₂Cl₂ / 24 h / Ambient temperature

2: neutral alumina / CH₂Cl₂ / 24 h

3: 80 percent / 40percent KF - alumina / acetonitrile / 24 h / Ambient temperature

4: LAH / diethyl ether / 1 h / 0 °C

5: Na₂CO₃ / diethyl ether / 3 h / 5 °C

6: 90 percent / activated MnO₂ / CHCl₃ / 5 h / Heating

7: 88 percent / diethyl ether / 1) -30 deg C, 30 min., 2) 0 deg C, 30 min., 3) r.t., 1 h

8: 90 percent / propane-1,3-dithiol, BF₃*Et₂O / CH₂Cl₂ / 1) -78 deg C, 2 h, 2) -40 deg C, 2 h, 3) 0 deg C, 1 h

9: 75 percent / DBU / CH₂Cl₂ / 0.67 h / 0 °C

10: 85 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

11: 84 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

12: 1) CF₃COOH, 2) Et₃N / 1) CH₂Cl₂, -70 -> -60 deg C, 3 h, 2) -60 -> 0 deg C, 1 h

13: 78 percent / 1) ZnCl₂, 2) Bu₃SnH / 2) Pd(PPh₃)4 / tetrahydrofuran / 1) r.t., 15 min., 2) 30 min

14: 73 percent / salcomine, O₂ / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; 1.3-propanedithiol; dmap; manganese(IV) oxide; aluminum oxide; potassium fluoride on basic alumina; lithium aluminium tetrahydride; salcomine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; oxygen; tri-n-butyl-tin hydride; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; acetonitrile;
DOI:10.1021/jo00028a045