Benzoic acid (1S,4R,4aS,5S,7S,8R,8aS)-4,5,8-triacetoxy-1-acetoxymethyl-7-hydroxy-3,6-dioxo-octahydro-isochromen-7-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (1S,4R,4aS,5S,7S,8R,8aS)-4,5,8-triacetoxy-1-acetoxymethyl-7-hydroxy-3,6-dioxo-octahydro-isochromen-7-ylmethyl ester
CAS No.:115944-89-3
Molecular Formula:C₂₆H₂₈O₁₄
Molecular Weight:564.5
Hs Code.:

Benzoic acid (1S,4R,4aS,5S,7S,8R,8aS)-4,5,8-triacetoxy-1-acetoxymethyl-7-hydroxy-3,6-dioxo-octahydro-isochromen-7-ylmethyl ester

Synonyms:

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Chemical Property of Benzoic acid (1S,4R,4aS,5S,7S,8R,8aS)-4,5,8-triacetoxy-1-acetoxymethyl-7-hydroxy-3,6-dioxo-octahydro-isochromen-7-ylmethyl ester

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Technology Process of Benzoic acid (1S,4R,4aS,5S,7S,8R,8aS)-4,5,8-triacetoxy-1-acetoxymethyl-7-hydroxy-3,6-dioxo-octahydro-isochromen-7-ylmethyl ester

There total 22 articles about Benzoic acid (1S,4R,4aS,5S,7S,8R,8aS)-4,5,8-triacetoxy-1-acetoxymethyl-7-hydroxy-3,6-dioxo-octahydro-isochromen-7-ylmethyl 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:

: 37112-31-5
levoglucosenone

: 115944-89-3
Benzoic acid (1S,4R,4aS,5S,7S,8R,8aS)-4,5,8-triacetoxy-1-acetoxymethyl-7-hydroxy-3,6-dioxo-octahydro-isochromen-7-ylmethyl ester

Guidance literature:: Multi-step reaction with 22 steps

1: 80 °C

2: NaBH₄

3: NaOCH₃

4: MnO₂

5: 96 percent / Br₂/(C₂H₅)3N / CH₂Cl₂ / 0 °C

6: 96 percent / NH₄Cl / ethanol / Ambient temperature

7: NaBH₄

8: camphorsulfonic acid

9: DIBAL-H / CH₂Cl₂; toluene

10: LiAlH₄ / tetrahydrofuran

11: pyridine

12: H₂O / acetic acid; H₂O; tetrahydrofuran

13: pyridine

14: 96 percent / trifluoroacetic acid/acetic anhydride

15: NH₂NH₂ / dimethylformamide

16: Jones ox.

17: 48 percent / SeO₂ / xylene

18: CrO₃/pyridine

19: NaBH₄/CeCl₃

20: pyridine

21: 1.) NMO, 2.)(CH₃CO)2O/pyridine / OsO₄ / acetonitrile/water

22: Swern ox.

With pyridine; chromium(VI) oxide; manganese(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; selenium(IV) oxide; N-methyl-2-indolinone; cerium(III) chloride; Jones ox; Swern ox; water; bromine; sodium methylate; acetic anhydride; diisobutylaluminium hydride; ammonium chloride; triethylamine; trifluoroacetic acid; hydrazine; osmium(VIII) oxide; camphor-10-sulfonic acid; In tetrahydrofuran; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; xylene;
DOI:10.1016/S0040-4039(00)96895-3

Reference yield:

: 113965-05-2
(1S,2S,6R,7S,8R,9R)-10,12-Dioxa-tricyclo[7.2.1.0^2,7]dodec-4-ene-6,8-diol

: 115944-89-3
Benzoic acid (1S,4R,4aS,5S,7S,8R,8aS)-4,5,8-triacetoxy-1-acetoxymethyl-7-hydroxy-3,6-dioxo-octahydro-isochromen-7-ylmethyl ester

Guidance literature:: Multi-step reaction with 19 steps

1: MnO₂

2: 96 percent / Br₂/(C₂H₅)3N / CH₂Cl₂ / 0 °C

3: 96 percent / NH₄Cl / ethanol / Ambient temperature

4: NaBH₄

5: camphorsulfonic acid

6: DIBAL-H / CH₂Cl₂; toluene

7: LiAlH₄ / tetrahydrofuran

8: pyridine

9: H₂O / acetic acid; H₂O; tetrahydrofuran

10: pyridine

11: 96 percent / trifluoroacetic acid/acetic anhydride

12: NH₂NH₂ / dimethylformamide

13: Jones ox.

14: 48 percent / SeO₂ / xylene

15: CrO₃/pyridine

16: NaBH₄/CeCl₃

17: pyridine

18: 1.) NMO, 2.)(CH₃CO)2O/pyridine / OsO₄ / acetonitrile/water

19: Swern ox.

With pyridine; chromium(VI) oxide; manganese(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; selenium(IV) oxide; N-methyl-2-indolinone; cerium(III) chloride; Jones ox; Swern ox; water; bromine; acetic anhydride; diisobutylaluminium hydride; ammonium chloride; triethylamine; trifluoroacetic acid; hydrazine; osmium(VIII) oxide; camphor-10-sulfonic acid; In tetrahydrofuran; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; xylene;
DOI:10.1016/S0040-4039(00)96895-3

Reference yield:

: 113965-06-3
(1S,2S,7R,8R,9R)-8-Hydroxy-10,12-dioxa-tricyclo[7.2.1.0^2,7]dodec-4-en-6-one

: 115944-89-3
Benzoic acid (1S,4R,4aS,5S,7S,8R,8aS)-4,5,8-triacetoxy-1-acetoxymethyl-7-hydroxy-3,6-dioxo-octahydro-isochromen-7-ylmethyl ester

Guidance literature:: Multi-step reaction with 18 steps

1: 96 percent / Br₂/(C₂H₅)3N / CH₂Cl₂ / 0 °C

2: 96 percent / NH₄Cl / ethanol / Ambient temperature

3: NaBH₄

4: camphorsulfonic acid

5: DIBAL-H / CH₂Cl₂; toluene

6: LiAlH₄ / tetrahydrofuran

7: pyridine

8: H₂O / acetic acid; H₂O; tetrahydrofuran

9: pyridine

10: 96 percent / trifluoroacetic acid/acetic anhydride

11: NH₂NH₂ / dimethylformamide

12: Jones ox.

13: 48 percent / SeO₂ / xylene

14: CrO₃/pyridine

15: NaBH₄/CeCl₃

16: pyridine

17: 1.) NMO, 2.)(CH₃CO)2O/pyridine / OsO₄ / acetonitrile/water

18: Swern ox.

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; selenium(IV) oxide; N-methyl-2-indolinone; cerium(III) chloride; Jones ox; Swern ox; water; bromine; acetic anhydride; diisobutylaluminium hydride; ammonium chloride; triethylamine; trifluoroacetic acid; hydrazine; osmium(VIII) oxide; camphor-10-sulfonic acid; In tetrahydrofuran; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; xylene;
DOI:10.1016/S0040-4039(00)96895-3