(2R,3R,4S,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3R,4S,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-ol
CAS No.:511511-29-8
Molecular Formula:C₁₇H₂₅N₃O₅
Molecular Weight:351.403
Hs Code.:

Synonyms:(2R,3R,4S,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3R,4S,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-ol

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Technology Process of (2R,3R,4S,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-ol

There total 4 articles about (2R,3R,4S,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-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: 86.0%

: 511511-38-9
[(2R,3R,4R,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

: 511511-29-8
(2R,3R,4S,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h;
DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2

Reference yield:

: [(2S,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yl]-acetaldehyde

: 511511-29-8
(2R,3R,4S,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 0.952 g / LiAlH₄ / tetrahydrofuran / 0.5 h

2: pyridine / CH₂Cl₂ / 16 h

3: NaN₃ / dimethylformamide / 3 h / 60 °C

4: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h

With pyridine; lithium aluminium tetrahydride; sodium azide; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2

Reference yield:

: 511511-37-8
2-[(2S,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yl]-ethanol

: 511511-29-8
(2R,3R,4S,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine / CH₂Cl₂ / 16 h

2: NaN₃ / dimethylformamide / 3 h / 60 °C

3: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h

With pyridine; sodium azide; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2