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

Base Information

Chemical Name:[(2S,3S,4S,5R,6R)-6-(3-Amino-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-yloxy]-acetic acid
CAS No.:193360-19-9
Molecular Formula:C₂₀H₃₁NO₈
Molecular Weight:413.468
Hs Code.:

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

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

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

There total 11 articles about [(2S,3S,4S,5R,6R)-6-(3-Amino-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-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:

: 193360-17-7
[(2S,3S,4S,5R,6R)-6-(3-Amino-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-yloxy]-acetic acid ethyl ester

: 193360-19-9
[(2S,3S,4S,5R,6R)-6-(3-Amino-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-yloxy]-acetic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; for 4h; Ambient temperature;
DOI:10.1016/S0040-4020(97)90389-6

Reference yield:

: 100-39-0
benzyl bromide

: 193360-19-9
[(2S,3S,4S,5R,6R)-6-(3-Amino-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-yloxy]-acetic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) n-Bu₂SnO, 2.) CsF / 1.) MeOH, 50 deg C, 4 h. 2.) DMF, rt, 14 h

2: 65 percent / NaH / tetrahydrofuran / 14 h / 0 - 20 °C

3: 83 percent / PPh₃ / tetrahydrofuran; H₂O / 4 h / 65 °C

4: LiOH*H₂O / tetrahydrofuran; H₂O / 4 h / Ambient temperature

With lithium hydroxide; sodium hydride; di(n-butyl)tin oxide; triphenylphosphine; cesium fluoride; In tetrahydrofuran; water;
DOI:10.1016/S0040-4020(97)90389-6

Reference yield:

: 131089-36-6
methyl 6-O-tert-butyldiphenylsilyl 2,3-O-isopropylidene-4-O-methyl-α-D-mannopyranoside

: 193360-19-9
[(2S,3S,4S,5R,6R)-6-(3-Amino-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-yloxy]-acetic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / TBAF / tetrahydrofuran / 14 h / 0 °C

2: 60 percent / NaH / tetrahydrofuran / 24 h / Ambient temperature

3: 85 percent / HCl / tetrahydrofuran; H₂O; acetic acid / 24 h / Ambient temperature

4: 1.) n-Bu₂SnO, 2.) CsF / 1.) MeOH, 50 deg C, 4 h. 2.) DMF, rt, 14 h

5: 65 percent / NaH / tetrahydrofuran / 14 h / 0 - 20 °C

6: 83 percent / PPh₃ / tetrahydrofuran; H₂O / 4 h / 65 °C

7: LiOH*H₂O / tetrahydrofuran; H₂O / 4 h / Ambient temperature

With hydrogenchloride; lithium hydroxide; tetrabutyl ammonium fluoride; sodium hydride; di(n-butyl)tin oxide; triphenylphosphine; cesium fluoride; In tetrahydrofuran; water; acetic acid;
DOI:10.1016/S0040-4020(97)90389-6