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

Base Information

Chemical Name:(2S,3S,4R,5R,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-ol
CAS No.:193360-13-3
Molecular Formula:C₁₈H₂₇N₃O₆
Molecular Weight:381.429
Hs Code.:

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

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Chemical Property of (2S,3S,4R,5R,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-ol

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Technology Process of (2S,3S,4R,5R,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-ol

There total 7 articles about (2S,3S,4R,5R,6R)-6-(3-Azido-propoxymethyl)-4-benzyloxy-2,5-dimethoxy-tetrahydro-pyran-3-ol 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:

: 131089-35-5
methyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside

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

Guidance literature:: Multi-step reaction with 5 steps

1: 69 percent / NaH, imidazole / tetrahydrofuran / 24 h / 0 °C

2: 92 percent / TBAF / tetrahydrofuran / 14 h / 0 °C

3: 60 percent / NaH / tetrahydrofuran / 24 h / Ambient temperature

4: 85 percent / HCl / tetrahydrofuran; H₂O; acetic acid / 24 h / Ambient temperature

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

With 1H-imidazole; hydrogenchloride; tetrabutyl ammonium fluoride; sodium hydride; di(n-butyl)tin oxide; cesium fluoride; In tetrahydrofuran; water; acetic acid;
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

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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

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