(2R,3S,4S,5R,6S)-5-((2S,4S,5S,6S)-4-Amino-5-hydroxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-(2,6-dimethoxy-phenoxy)-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

Base Information

Chemical Name:(2R,3S,4S,5R,6S)-5-((2S,4S,5S,6S)-4-Amino-5-hydroxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-(2,6-dimethoxy-phenoxy)-2-hydroxymethyl-tetrahydro-pyran-3,4-diol
CAS No.:216668-80-3
Molecular Formula:C₂₁H₃₃NO₁₀
Molecular Weight:459.494
Hs Code.:

(2R,3S,4S,5R,6S)-5-((2S,4S,5S,6S)-4-Amino-5-hydroxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-(2,6-dimethoxy-phenoxy)-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

Synonyms:(2R,3S,4S,5R,6S)-5-((2S,4S,5S,6S)-4-Amino-5-hydroxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-(2,6-dimethoxy-phenoxy)-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

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Chemical Property of (2R,3S,4S,5R,6S)-5-((2S,4S,5S,6S)-4-Amino-5-hydroxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-(2,6-dimethoxy-phenoxy)-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

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Technology Process of (2R,3S,4S,5R,6S)-5-((2S,4S,5S,6S)-4-Amino-5-hydroxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-(2,6-dimethoxy-phenoxy)-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

There total 14 articles about (2R,3S,4S,5R,6S)-5-((2S,4S,5S,6S)-4-Amino-5-hydroxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-(2,6-dimethoxy-phenoxy)-2-hydroxymethyl-tetrahydro-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: 73.0%

: 283154-38-1
{(2S,3S,4S,6S)-6-[(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-3-hydroxy-2,4-dimethyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester

: 216668-80-3
(2R,3S,4S,5R,6S)-5-((2S,4S,5S,6S)-4-Amino-5-hydroxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-(2,6-dimethoxy-phenoxy)-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

Guidance literature:: With hydrogen; palladium dihydroxide; In methanol; for 1h;
DOI:10.1021/ja982414m

Reference yield:

: 135192-43-7
2,6-dimethoxyphenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside

: 216668-80-3
(2R,3S,4S,5R,6S)-5-((2S,4S,5S,6S)-4-Amino-5-hydroxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-(2,6-dimethoxy-phenoxy)-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / 4 Angstroem MS; BF₃*Et₂O; TMSOTf / CH₂Cl₂ / 72 h / -30 - 25 °C

2: H₂ / 10 percent Pd/C / ethyl acetate / 12 h / 25 °C

With trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; boron trifluoride diethyl etherate; hydrogen; palladium on activated charcoal; In dichloromethane; ethyl acetate; 1: Condensation / 2: Hydrogenolysis;
DOI:10.1002/(SICI)1521-3765(19990903)5:9<2648::AID-CHEM2648>3.0.CO;2-Q

Reference yield:

: {(2S,3S,4S,6S)-3-Benzyloxy-6-[(2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-2,4-dimethyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester

: 216668-80-3
(2R,3S,4S,5R,6S)-5-((2S,4S,5S,6S)-4-Amino-5-hydroxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-(2,6-dimethoxy-phenoxy)-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; at 25 ℃; for 12h;
DOI:10.1002/(SICI)1521-3765(19990903)5:9<2648::AID-CHEM2648>3.0.CO;2-Q