4-Azido-butyric acid (2R,3R,4S,5R,6R)-3,5-bis-(4-azido-butyryloxy)-2-hydroxymethyl-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-4-yl ester

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Chemical Name:4-Azido-butyric acid (2R,3R,4S,5R,6R)-3,5-bis-(4-azido-butyryloxy)-2-hydroxymethyl-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-4-yl ester
CAS No.:184648-46-2
Molecular Formula:C₃₀H₄₃N₉O₁₁
Molecular Weight:705.725
Hs Code.:

4-Azido-butyric acid (2R,3R,4S,5R,6R)-3,5-bis-(4-azido-butyryloxy)-2-hydroxymethyl-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-4-yl ester

Synonyms:4-Azido-butyric acid (2R,3R,4S,5R,6R)-3,5-bis-(4-azido-butyryloxy)-2-hydroxymethyl-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-4-yl ester

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Chemical Property of 4-Azido-butyric acid (2R,3R,4S,5R,6R)-3,5-bis-(4-azido-butyryloxy)-2-hydroxymethyl-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-4-yl ester

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Technology Process of 4-Azido-butyric acid (2R,3R,4S,5R,6R)-3,5-bis-(4-azido-butyryloxy)-2-hydroxymethyl-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-4-yl ester

There total 8 articles about 4-Azido-butyric acid (2R,3R,4S,5R,6R)-3,5-bis-(4-azido-butyryloxy)-2-hydroxymethyl-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-4-yl 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: 83.0%

: 184648-45-1
4-Azido-butyric acid (2R,3R,4S,5R,6R)-3,5-bis-(4-azido-butyryloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-4-yl ester

: 184648-46-2
4-Azido-butyric acid (2R,3R,4S,5R,6R)-3,5-bis-(4-azido-butyryloxy)-2-hydroxymethyl-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-4-yl ester

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; Ambient temperature;
DOI:10.1021/jo961623r

Reference yield:

: 81058-27-7
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

: 184648-46-2
4-Azido-butyric acid (2R,3R,4S,5R,6R)-3,5-bis-(4-azido-butyryloxy)-2-hydroxymethyl-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 83 percent / 4 Angstroem molecular sieves, Ag₂CO₃ / diethyl ether / 48 h

2: 95 percent / H₂ / Pd-C / methanol / 5 h

3: 93 percent / BF₃*THF / tetrahydrofuran / 1) 0 deg C, 30 min, 2) 0 deg C -> room temperature, 30 min

4: TfOH / diethyl ether / 2 h / Ambient temperature

5: 2.39 g / NaOH / H₂O; ethanol / 36 h

6: 92 percent / imidazole / CH₂Cl₂ / 24 h / 0 °C

7: 86 percent / pyridine / CH₂Cl₂ / 6 h / 0 °C

8: 83 percent / HF-pyridine / tetrahydrofuran / Ambient temperature

With pyridine; 1H-imidazole; sodium hydroxide; boron trifluoride-tetrahydrofuran complex; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrogen; pyridine hydrogenfluoride; silver carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water;
DOI:10.1021/jo961623r

Reference yield:

: 184648-40-6
(S)-3-[(2R,3R,4S,5R,6R)-3,4,5-Tris-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-2-yloxy]-butyric acid benzyl ester

: 184648-46-2
4-Azido-butyric acid (2R,3R,4S,5R,6R)-3,5-bis-(4-azido-butyryloxy)-2-hydroxymethyl-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / H₂ / Pd-C / methanol / 5 h

2: 93 percent / BF₃*THF / tetrahydrofuran / 1) 0 deg C, 30 min, 2) 0 deg C -> room temperature, 30 min

3: TfOH / diethyl ether / 2 h / Ambient temperature

4: 2.39 g / NaOH / H₂O; ethanol / 36 h

5: 92 percent / imidazole / CH₂Cl₂ / 24 h / 0 °C

6: 86 percent / pyridine / CH₂Cl₂ / 6 h / 0 °C

7: 83 percent / HF-pyridine / tetrahydrofuran / Ambient temperature

With pyridine; 1H-imidazole; sodium hydroxide; boron trifluoride-tetrahydrofuran complex; trifluorormethanesulfonic acid; hydrogen; pyridine hydrogenfluoride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water;
DOI:10.1021/jo961623r