(2S,3R,4R,5S,6S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran

Base Information

Chemical Name:(2S,3R,4R,5S,6S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran
CAS No.:97989-92-9
Molecular Formula:C₃₇H₄₉NO₁₁
Molecular Weight:683.796
Hs Code.:

(2S,3R,4R,5S,6S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran

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Chemical Property of (2S,3R,4R,5S,6S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran

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Technology Process of (2S,3R,4R,5S,6S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran

There total 100 articles about (2S,3R,4R,5S,6S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran 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%

: 120042-03-7,120042-04-8,120042-05-9,120063-45-8
(2R,3R,4R,5S,6RS)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-6-hydroxy-4-(N-methoxycarbonyl-N-methylamino)-3,5-bis(methoxymethyloxy)-2-methyltetrahydropyran

: 107-30-2
chloromethyl methyl ether

: 97989-92-9,120042-06-0,120042-07-1,120063-44-7
[(2R,3R,4R,5S)-2-(2,5-Bis-benzyloxy-3,4-dimethyl-phenyl)-3,5,6-tris-methoxymethoxy-2-methyl-tetrahydro-pyran-4-yl]-methyl-carbamic acid methyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 12h; Heating;
DOI:10.1016/S0040-4039(00)98139-5

Reference yield:

: 67412-71-9
(-)-benzyl 2,3-anhydro-β-D-ribopyranoside

: 97989-92-9,120042-06-0,120042-07-1,120063-44-7
(2R,3R,4R,5S,6R)-(+)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran

Guidance literature:: Multi-step reaction with 11 steps

1: 100 percent / methanol / 24 h / 60 °C

2: 85 percent / anhydrous K₂CO₃ / acetone / 1 h / Heating

3: 97 percent / ethyldiisopropylamine / tetrahydrofuran / 0.5 h / Heating

4: 99 percent / H₂, 12 M HCl / 10 percent Pd-C / ethanol / 10 h / Ambient temperature

5: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 10 min; 2.) CH₂Cl₂, -60 deg C to -20 deg C, 30 min

6: 94 percent / tetrahydrofuran; hexane / 2 h / -78 °C

7: 84 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

8: 1.) 1.5 M butyllithium / 1.) hexane, ether, 0 deg C, 10 min; 2.) THF, hexane, ether, 0 deg C, 1 min; variation of reagents, solvent, reaction time and temperature

9: 94 percent / 1.0 M Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

10: 88 percent / sulfur trioxide pyridine complex (SO₃Py), DMSO, triethylamine / tetrahydrofuran / 2 h / Ambient temperature

11: 85 percent / ethyldiisopropylamine / tetrahydrofuran / 12 h / Heating

With 1H-imidazole; hydrogenchloride; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; sulfur trioxide pyridine complex; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(01)81431-9

Reference yield:

: 67412-71-9
(-)-benzyl 2,3-anhydro-β-D-ribopyranoside

: 97989-92-9,120042-06-0,120042-07-1,120063-44-7
(2R,3R,4R,5S,6S)-(+)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-4-(N-methoxycarbonyl-N-methylamino)-3,5,6-tris(methoxymethyloxy)-2-methyltetrahydropyran

Guidance literature:: Multi-step reaction with 11 steps

1: 100 percent / methanol / 24 h / 60 °C

2: 85 percent / anhydrous K₂CO₃ / acetone / 1 h / Heating

3: 97 percent / ethyldiisopropylamine / tetrahydrofuran / 0.5 h / Heating

4: 99 percent / H₂, 12 M HCl / 10 percent Pd-C / ethanol / 10 h / Ambient temperature

5: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 10 min; 2.) CH₂Cl₂, -60 deg C to -20 deg C, 30 min

6: 94 percent / tetrahydrofuran; hexane / 2 h / -78 °C

7: 84 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

8: 1.) 1.5 M butyllithium / 1.) hexane, ether, 0 deg C, 10 min; 2.) THF, hexane, ether, 0 deg C, 1 min; variation of reagents, solvent, reaction time and temperature

9: 94 percent / 1.0 M Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

10: 88 percent / sulfur trioxide pyridine complex (SO₃Py), DMSO, triethylamine / tetrahydrofuran / 2 h / Ambient temperature

11: 6 percent / ethyldiisopropylamine / tetrahydrofuran / 12 h / Heating

With 1H-imidazole; hydrogenchloride; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; sulfur trioxide pyridine complex; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(01)81431-9