(1R,2S,3R,4R,5S,6S)-4-Azido-3,5-bis-benzyloxy-7-oxa-bicyclo[4.1.0]heptan-2-ol

Base Information

Chemical Name:(1R,2S,3R,4R,5S,6S)-4-Azido-3,5-bis-benzyloxy-7-oxa-bicyclo[4.1.0]heptan-2-ol
CAS No.:151071-17-9
Molecular Formula:C₂₀H₂₁N₃O₄
Molecular Weight:367.404
Hs Code.:

Synonyms:(1R,2S,3R,4R,5S,6S)-4-Azido-3,5-bis-benzyloxy-7-oxa-bicyclo[4.1.0]heptan-2-ol

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Chemical Property of (1R,2S,3R,4R,5S,6S)-4-Azido-3,5-bis-benzyloxy-7-oxa-bicyclo[4.1.0]heptan-2-ol

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Technology Process of (1R,2S,3R,4R,5S,6S)-4-Azido-3,5-bis-benzyloxy-7-oxa-bicyclo[4.1.0]heptan-2-ol

There total 13 articles about (1R,2S,3R,4R,5S,6S)-4-Azido-3,5-bis-benzyloxy-7-oxa-bicyclo[4.1.0]heptan-2-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:

: (1S,2S,3R,4R,5S,6S)-3-Azido-2,4-bis-benzyloxy-5-(4-methoxy-benzyloxy)-7-oxa-bicyclo[4.1.0]heptane

: 151071-17-9
(1R,2S,3R,4R,5S,6S)-4-Azido-3,5-bis-benzyloxy-7-oxa-bicyclo[4.1.0]heptan-2-ol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; Yield given; Ambient temperature;
DOI:10.1016/S0040-4039(00)73653-7

Reference yield:

: 100-39-0
benzyl bromide

: 151071-17-9
(1R,2S,3R,4R,5S,6S)-4-Azido-3,5-bis-benzyloxy-7-oxa-bicyclo[4.1.0]heptan-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran / Ambient temperature

2: DDQ / CH₂Cl₂; H₂O / Ambient temperature

With sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/S0040-4039(00)73653-7

Reference yield:

: 142012-05-3
(1R,2S,3R,4S)-4-butyryloxy-2,3-isopropylidenedioxy-5-cyclohexen-1-ol

: 151071-17-9
(1R,2S,3R,4R,5S,6S)-4-Azido-3,5-bis-benzyloxy-7-oxa-bicyclo[4.1.0]heptan-2-ol

Guidance literature:: Multi-step reaction with 12 steps

1: CSA / CH₂Cl₂ / 24 h / Ambient temperature

2: K₂CO₃ / methanol / Ambient temperature

3: PPh₃, DEAD / tetrahydrofuran / Ambient temperature

4: K₂CO₃ / methanol / Ambient temperature

5: imidazole / dimethylformamide / 45 °C

6: 90 percent / PPTS / methanol / 12 h / 45 °C

7: 89 percent / SO₂Cl₂, NEt₃ / CH₂Cl₂ / 12 h / Ambient temperature

9: TBAF / tetrahydrofuran / Ambient temperature

10: mCPBA / CH₂Cl₂ / 72 h / Ambient temperature

11: NaH / tetrahydrofuran / Ambient temperature

12: DDQ / CH₂Cl₂; H₂O / Ambient temperature

With 1H-imidazole; sulfuryl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)73653-7