[(2S,4R,5S,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid methyl ester

Base Information

Chemical Name:[(2S,4R,5S,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid methyl ester
CAS No.:193360-30-4
Molecular Formula:C₂₀H₂₉N₃O₇
Molecular Weight:423.466
Hs Code.:

Synonyms:[(2S,4R,5S,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid methyl ester

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Chemical Property of [(2S,4R,5S,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid methyl ester

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Technology Process of [(2S,4R,5S,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid methyl ester

There total 6 articles about [(2S,4R,5S,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid methyl ester 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: 66.0%

: 193360-44-0
3-azidopropyl trifluoromethanesulfonate

: 193360-28-0
((2S,4R,5S,6R)-4-Benzyloxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yloxy)-acetic acid methyl ester

: 193360-30-4
[(2S,4R,5S,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid methyl ester

Guidance literature:: With sodium hydride; In dichloromethane; for 14h; Ambient temperature;
DOI:10.1016/S0040-4020(97)90389-6

Reference yield:

: 87316-22-1
(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

: 193360-30-4
[(2S,4R,5S,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) n-Bu₂SnO, 2.) n-Bu₄NBr / 1.) TolH, reflux, 4 h, 2.) TolH, 80 deg C, 18 h

2: 88 percent / NaH / benzene / 14 h / Heating

3: 75 percent / PPh₃*HBr / CH₂Cl₂ / 3 h / Ambient temperature

4: 79 percent / TBAF / tetrahydrofuran / 10 h / Ambient temperature

5: 66 percent / NaH / CH₂Cl₂ / 14 h / Ambient temperature

With tetrabutyl ammonium fluoride; tetrabutylammomium bromide; triphenylphosphine hydrobromide; sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1016/S0040-4020(97)90389-6

Reference yield:

: 100-39-0
benzyl bromide

: 193360-30-4
[(2S,4R,5S,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) n-Bu₂SnO, 2.) n-Bu₄NBr / 1.) TolH, reflux, 4 h, 2.) TolH, 80 deg C, 18 h

2: 88 percent / NaH / benzene / 14 h / Heating

3: 75 percent / PPh₃*HBr / CH₂Cl₂ / 3 h / Ambient temperature

4: 79 percent / TBAF / tetrahydrofuran / 10 h / Ambient temperature

5: 66 percent / NaH / CH₂Cl₂ / 14 h / Ambient temperature

With tetrabutyl ammonium fluoride; tetrabutylammomium bromide; triphenylphosphine hydrobromide; sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1016/S0040-4020(97)90389-6