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

Base Information

Chemical Name:Acetic acid (2S,3R,4R,5R,6R)-6-((S)-2-acetoxy-1-benzyloxy-ethyl)-5-azido-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl ester
CAS No.:272775-95-8
Molecular Formula:C₃₂H₃₅N₃O₈
Molecular Weight:589.645
Hs Code.:

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

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Chemical Property of Acetic acid (2S,3R,4R,5R,6R)-6-((S)-2-acetoxy-1-benzyloxy-ethyl)-5-azido-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl ester

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Technology Process of Acetic acid (2S,3R,4R,5R,6R)-6-((S)-2-acetoxy-1-benzyloxy-ethyl)-5-azido-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl ester

There total 24 articles about Acetic acid (2S,3R,4R,5R,6R)-6-((S)-2-acetoxy-1-benzyloxy-ethyl)-5-azido-3,4-bis-benzyloxy-tetrahydro-pyran-2-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:

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

: 272775-95-8
Acetic acid (2S,3R,4R,5R,6R)-6-((S)-2-acetoxy-1-benzyloxy-ethyl)-5-azido-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 23 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

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; sodium azide; 18-crown-6 ether; water; 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; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 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;
DOI:10.1021/ol005715l

Reference yield:

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

: 272775-95-8
Acetic acid (2S,3R,4R,5R,6R)-6-((S)-2-acetoxy-1-benzyloxy-ethyl)-5-azido-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 22 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

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; sodium azide; 18-crown-6 ether; water; 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; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 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;
DOI:10.1021/ol005715l

Reference yield:

: 87-89-8
D-myo-inositol

: 272775-95-8
Acetic acid (2S,3R,4R,5R,6R)-6-((S)-2-acetoxy-1-benzyloxy-ethyl)-5-azido-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 24 steps

1: p-TsOH / dimethylformamide

2: NaH / dimethylformamide

3: p-TsOH / ethanol / 45 °C

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

5: aq. AcOH / 50 °C

6: 41 percent / DCC; DMAP / CH₂Cl₂ / -20 °C

7: 85 percent / NaOMe / methanol / 50 °C

8: pyridine / 20 °C

9: pyridine / 20 °C

10: NaN₃ / dimethylformamide / 100 °C

11: NaOMe / methanol / 20 °C

12: pyridine / 20 °C

13: 18-crown-6 / dimethylformamide / 100 °C

14: DDQ; H₂O / CH₂Cl₂ / 0 °C

15: NaOMe / methanol / 20 °C

16: NaIO₄ / H₂O; methanol / 20 °C

17: NaBH₄ / methanol / 0 °C

18: p-TsOH / dimethylformamide / 20 °C

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

20: diethyl ether / -115 °C

21: NaH / dimethylformamide / 0 °C

22: O₃ / CH₂Cl₂ / -78 °C

23: p-TsOH / methanol / 0 °C

24: pyridine / 20 °C

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; sodium azide; 18-crown-6 ether; water; 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; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1: Condensation / 2: Etherification / 3: Substitution / 4: Etherification / 5: Hydrolysis / 6: Acylation / 7: deacylation / 8: Acylation / 9: mesylation / 10: Substitution / 11: deacylation / 12: mesylation / 13: Acetoxylation / 14: Substitution / 15: Deacetylation / 16: Oxidation / 17: Reduction / 18: Condensation / 19: Moffatt oxidation / 20: Addition / 21: Etherification / 22: ozonolysis / 23: Hydrolysis / 24: Acetylation;
DOI:10.1021/ol005715l