Acetic acid (S)-2-((2R,3R,4R,5R,6S)-6-amino-3-azido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yl)-2-benzyloxy-ethyl ester

Base Information

Chemical Name:Acetic acid (S)-2-((2R,3R,4R,5R,6S)-6-amino-3-azido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yl)-2-benzyloxy-ethyl ester
CAS No.:272775-98-1
Molecular Formula:C₃₀H₃₄N₄O₆
Molecular Weight:546.623
Hs Code.:

Synonyms:Acetic acid (S)-2-((2R,3R,4R,5R,6S)-6-amino-3-azido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yl)-2-benzyloxy-ethyl ester

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Chemical Property of Acetic acid (S)-2-((2R,3R,4R,5R,6S)-6-amino-3-azido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yl)-2-benzyloxy-ethyl ester

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Technology Process of Acetic acid (S)-2-((2R,3R,4R,5R,6S)-6-amino-3-azido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yl)-2-benzyloxy-ethyl ester

There total 26 articles about Acetic acid (S)-2-((2R,3R,4R,5R,6S)-6-amino-3-azido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yl)-2-benzyloxy-ethyl 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: 78.0%

: 272775-97-0
Acetic acid (S)-2-benzyloxy-2-((2R,3R,4R,5R,6S)-3,6-diazido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yl)-ethyl ester

: 272775-98-1
Acetic acid (S)-2-((2R,3R,4R,5R,6S)-6-amino-3-azido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yl)-2-benzyloxy-ethyl ester

Guidance literature:: With hydrogen; Lindlar's catalyst; In toluene; at 20 ℃; under 760.051 Torr;
DOI:10.1021/ol005715l

Reference yield:

: (±)-1,2:4,5-di-O-cyclohexylidene-myo-inositol

: 272775-98-1
Acetic acid (S)-2-((2R,3R,4R,5R,6S)-6-amino-3-azido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yl)-2-benzyloxy-ethyl ester

Guidance literature:: Multi-step reaction with 26 steps

1: NaH / dimethylformamide

2: p-TsOH / ethanol / 45 °C

3: NaH; Bu₄NI / tetrahydrofuran; dimethylformamide / 20 °C

4: aq. AcOH / 50 °C

5: 41 percent / DCC; DMAP / CH₂Cl₂ / -20 °C

6: 85 percent / NaOMe / methanol / 50 °C

7: pyridine / 20 °C

8: pyridine / 20 °C

9: NaN₃ / dimethylformamide / 100 °C

10: NaOMe / methanol / 20 °C

11: pyridine / 20 °C

12: 18-crown-6 / dimethylformamide / 100 °C

13: DDQ; H₂O / CH₂Cl₂ / 0 °C

14: NaOMe / methanol / 20 °C

15: NaIO₄ / H₂O; methanol / 20 °C

16: NaBH₄ / methanol / 0 °C

17: p-TsOH / dimethylformamide / 20 °C

18: DMSO; DCC; TFA / pyridine; benzene / 20 °C

19: diethyl ether / -115 °C

20: NaH / dimethylformamide / 0 °C

21: O₃ / CH₂Cl₂ / -78 °C

22: p-TsOH / methanol / 0 °C

23: pyridine / 20 °C

24: trimethylsilyl bromide / CHCl₃ / 20 °C

25: trimethylsilyl azide; Bu₄NF / tetrahydrofuran / 20 °C

26: 78 percent / H₂ / Lindlar catalyst / toluene / 20 °C / 760.05 Torr

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; sodium azide; 18-crown-6 ether; trimethylsilyl bromide; trimethylsilylazide; tetrabutyl ammonium fluoride; water; hydrogen; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; ozone; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; benzene; 1: Etherification / 2: Substitution / 3: Etherification / 4: Hydrolysis / 5: Acylation / 6: deacylation / 7: Acylation / 8: mesylation / 9: Substitution / 10: deacylation / 11: mesylation / 12: Acetoxylation / 13: Substitution / 14: Deacetylation / 15: Oxidation / 16: Reduction / 17: Condensation / 18: Moffatt oxidation / 19: Addition / 20: Etherification / 21: ozonolysis / 22: Hydrolysis / 23: Acetylation / 24: Substitution / 25: Substitution / 26: Hydrogenation;
DOI:10.1021/ol005715l

Reference yield:

: (±)-1,4-di-O-benzyl-2,3:5,6-di-O-cyclohexylidene-myo-inositol

: 272775-98-1
Acetic acid (S)-2-((2R,3R,4R,5R,6S)-6-amino-3-azido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yl)-2-benzyloxy-ethyl ester

Guidance literature:: Multi-step reaction with 25 steps

1: p-TsOH / ethanol / 45 °C

2: NaH; Bu₄NI / tetrahydrofuran; dimethylformamide / 20 °C

3: aq. AcOH / 50 °C

4: 41 percent / DCC; DMAP / CH₂Cl₂ / -20 °C

5: 85 percent / NaOMe / methanol / 50 °C

6: pyridine / 20 °C

7: pyridine / 20 °C

8: NaN₃ / dimethylformamide / 100 °C

9: NaOMe / methanol / 20 °C

10: pyridine / 20 °C

11: 18-crown-6 / dimethylformamide / 100 °C

12: DDQ; H₂O / CH₂Cl₂ / 0 °C

13: NaOMe / methanol / 20 °C

14: NaIO₄ / H₂O; methanol / 20 °C

15: NaBH₄ / methanol / 0 °C

16: p-TsOH / dimethylformamide / 20 °C

17: DMSO; DCC; TFA / pyridine; benzene / 20 °C

18: diethyl ether / -115 °C

19: NaH / dimethylformamide / 0 °C

20: O₃ / CH₂Cl₂ / -78 °C

21: p-TsOH / methanol / 0 °C

22: pyridine / 20 °C

23: trimethylsilyl bromide / CHCl₃ / 20 °C

24: trimethylsilyl azide; Bu₄NF / tetrahydrofuran / 20 °C

25: 78 percent / H₂ / Lindlar catalyst / toluene / 20 °C / 760.05 Torr

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; sodium azide; 18-crown-6 ether; trimethylsilyl bromide; trimethylsilylazide; tetrabutyl ammonium fluoride; water; hydrogen; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; ozone; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; benzene; 1: Substitution / 2: Etherification / 3: Hydrolysis / 4: Acylation / 5: deacylation / 6: Acylation / 7: mesylation / 8: Substitution / 9: deacylation / 10: mesylation / 11: Acetoxylation / 12: Substitution / 13: Deacetylation / 14: Oxidation / 15: Reduction / 16: Condensation / 17: Moffatt oxidation / 18: Addition / 19: Etherification / 20: ozonolysis / 21: Hydrolysis / 22: Acetylation / 23: Substitution / 24: Substitution / 25: Hydrogenation;
DOI:10.1021/ol005715l