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

Base Information

Chemical Name:[(2S,4R,5S,6R)-6-(3-Amino-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid
CAS No.:193360-33-7
Molecular Formula:C₁₉H₂₉NO₇
Molecular Weight:383.442
Hs Code.:

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

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

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

There total 8 articles about [(2S,4R,5S,6R)-6-(3-Amino-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid 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:

: 193360-32-6
[(2S,4R,5S,6R)-6-(3-Amino-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid methyl ester

: 193360-33-7
[(2S,4R,5S,6R)-6-(3-Amino-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; for 4h;
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

: 193360-33-7
[(2S,4R,5S,6R)-6-(3-Amino-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid

Guidance literature:: Multi-step reaction with 7 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

6: 77 percent / PPh₃ / tetrahydrofuran; H₂O / 5 h / 65 °C

7: LiOH / tetrahydrofuran; H₂O / 4 h

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

Reference yield:

: 100-39-0
benzyl bromide

: 193360-33-7
[(2S,4R,5S,6R)-6-(3-Amino-propoxymethyl)-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid

Guidance literature:: Multi-step reaction with 7 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

6: 77 percent / PPh₃ / tetrahydrofuran; H₂O / 5 h / 65 °C

7: LiOH / tetrahydrofuran; H₂O / 4 h

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