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

Base Information

Chemical Name:[(2S,3S,4S,5R,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-yloxy]-acetic acid ethyl ester
CAS No.:193360-15-5
Molecular Formula:C₂₂H₃₃N₃O₈
Molecular Weight:467.519
Hs Code.:

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

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

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

There total 9 articles about [(2S,3S,4S,5R,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-yloxy]-acetic acid ethyl 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: 65.0%

: 105-36-2
ethyl bromoacetate

: 193360-13-3
(2S,3S,4R,5R,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-ol

: 193360-15-5
[(2S,3S,4S,5R,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-yloxy]-acetic acid ethyl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 14h;
DOI:10.1016/S0040-4020(97)90389-6

Reference yield:

: 100-39-0
benzyl bromide

: 193360-15-5
[(2S,3S,4S,5R,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-yloxy]-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 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

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

Reference yield:

: 82185-76-0
methyl 2,3-O-isopropylidene-4-O-methyl-α-D-mannopyranoside

: 193360-15-5
[(2S,3S,4S,5R,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-yloxy]-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 60 percent / NaH / tetrahydrofuran / 24 h / Ambient temperature

2: 85 percent / HCl / tetrahydrofuran; H₂O; acetic acid / 24 h / Ambient temperature

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

4: 65 percent / NaH / tetrahydrofuran / 14 h / 0 - 20 °C

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