(2S,3S,4S,5R,6S)-3-Azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Base Information

Chemical Name:(2S,3S,4S,5R,6S)-3-Azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde
CAS No.:74844-36-3
Molecular Formula:C₂₁H₂₃N₃O₅
Molecular Weight:397.431
Hs Code.:

Synonyms:(2S,3S,4S,5R,6S)-3-Azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

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Chemical Property of (2S,3S,4S,5R,6S)-3-Azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

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Technology Process of (2S,3S,4S,5R,6S)-3-Azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

There total 5 articles about (2S,3S,4S,5R,6S)-3-Azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde 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: 87.0%

: 74844-35-2
2-((2S,3R,4S,5R,6S)-3-Azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-1,3-diphenyl-imidazolidine

: 74844-36-3
(2S,3S,4S,5R,6S)-3-Azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; 1.) 0 deg C, 0.5 h; 2.) 3.5 h, room temperature;
DOI:10.1021/jo01310a060

Reference yield:

: 29388-46-3
methyl 2,3-di-O-benzyl-α-D-galactopyranoside

: 74844-36-3
(2S,3S,4S,5R,6S)-3-Azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) Pyridine, 75 deg C, 18 h; 2.) 0 deg C to room temperature, 2 days

2: 4:1 acetic acid, water / 4 h / 100 °C

3: 92 percent / sodium azide / dimethylformamide / 5 h / 120 °C

4: dicyclohexylcarbodiimide / 1.) DMSO, oxidation; 2.) methanol, room temp., 24 h

5: 87 percent / aq. HCl / tetrahydrofuran / 1.) 0 deg C, 0.5 h; 2.) 3.5 h, room temperature

With hydrogenchloride; sodium azide; water; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo01310a060

Reference yield:

: 71756-39-3
methyl 2,3-di-O-benzyl-4-O-mesyl-6-O-trityl-α-D-galactopyranoside

: 74844-36-3
(2S,3S,4S,5R,6S)-3-Azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 4:1 acetic acid, water / 4 h / 100 °C

2: 92 percent / sodium azide / dimethylformamide / 5 h / 120 °C

3: dicyclohexylcarbodiimide / 1.) DMSO, oxidation; 2.) methanol, room temp., 24 h

4: 87 percent / aq. HCl / tetrahydrofuran / 1.) 0 deg C, 0.5 h; 2.) 3.5 h, room temperature

With hydrogenchloride; sodium azide; water; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo01310a060