(2R,3R,4S,5S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-2-hexanol

Base Information

Chemical Name:(2R,3R,4S,5S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-2-hexanol
CAS No.:97989-87-2
Molecular Formula:C₄₁H₆₁NO₁₀Si
Molecular Weight:756.022
Hs Code.:

(2R,3R,4S,5S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-2-hexanol

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Chemical Property of (2R,3R,4S,5S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-2-hexanol

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Technology Process of (2R,3R,4S,5S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-2-hexanol

There total 38 articles about (2R,3R,4S,5S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-2-hexanol 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: 90.0%

: 94616-84-9
dichloromethylcerium

: {(1S,2R)-3-(2,5-Bis-benzyloxy-3,4-dimethyl-phenyl)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-2-methoxymethoxy-3-oxo-propyl}-methyl-carbamic acid methyl ester

: 97989-87-2,97989-88-3
(2S,3R,4S,5S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-2-hexanol

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1016/S0040-4020(01)81431-9

Reference yield:

: 97989-81-6
(-)-benzyl β-D-gentosaminide

: 97989-87-2,97989-88-3
(2S,3R,4S,5S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-2-hexanol

Guidance literature:: Multi-step reaction with 7 steps

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

2: 97 percent / ethyldiisopropylamine / tetrahydrofuran / 0.5 h / Heating

3: 99 percent / H₂, 12 M HCl / 10 percent Pd-C / ethanol / 10 h / Ambient temperature

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

5: 94 percent / tetrahydrofuran; hexane / 2 h / -78 °C

6: 84 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

7: 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

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

Reference yield:

: 97989-81-6
(-)-benzyl β-D-gentosaminide

: 97989-87-2,97989-88-3
(2R,3R,4S,5S)-(-)-2-(2,5-dibenzyloxy-3,4-dimethylphenyl)-6-(tert-butyldimethylsilyloxy)-4-(N-methoxycarbonyl-N-methylamino)-2,4-bis(methoxymethyloxy)-2-hexanol

Guidance literature:: Multi-step reaction with 7 steps

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

2: 97 percent / ethyldiisopropylamine / tetrahydrofuran / 0.5 h / Heating

3: 99 percent / H₂, 12 M HCl / 10 percent Pd-C / ethanol / 10 h / Ambient temperature

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

5: 94 percent / tetrahydrofuran; hexane / 2 h / -78 °C

6: 84 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

7: 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

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