(1S,2S,3R,4R,5R,6S)-2-exo,4-endo-bis(acetyloxy)-6-endo-(benzyloxy)-7-oxo-8-oxabicyclo[3.2.1]oct-3-endo-yl benzoate

Base Information

• Chemical Name: (1S,2S,3R,4R,5R,6S)-2-exo,4-endo-bis(acetyloxy)-6-endo-(benzyloxy)-7-oxo-8-oxabicyclo[3.2.1]oct-3-endo-yl benzoate
• CAS No.: 223677-27-8
• Molecular Formula: C₂₅H₂₄O₉
• Molecular Weight: 468.46

Synonyms:(1S,2S,3R,4R,5R,6S)-2-exo,4-endo-bis(acetyloxy)-6-endo-(benzyloxy)-7-oxo-8-oxabicyclo[3.2.1]oct-3-endo-yl benzoate

Chemical Property of (1S,2S,3R,4R,5R,6S)-2-exo,4-endo-bis(acetyloxy)-6-endo-(benzyloxy)-7-oxo-8-oxabicyclo[3.2.1]oct-3-endo-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (1S,2S,3R,4R,5R,6S)-2-exo,4-endo-bis(acetyloxy)-6-endo-(benzyloxy)-7-oxo-8-oxabicyclo[3.2.1]oct-3-endo-yl benzoate

There total 19 articles about (1S,2S,3R,4R,5R,6S)-2-exo,4-endo-bis(acetyloxy)-6-endo-(benzyloxy)-7-oxo-8-oxabicyclo[3.2.1]oct-3-endo-yl benzoate 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:

(+/-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one (115140-20-0,129829-54-5,139342-54-4) → (1S,2S,3R,4R,5R,6S)-2-exo,4-endo-bis(acetyloxy)-6-endo-(benzyloxy)-7-oxo-8-oxabicyclo[3.2.1]oct-3-endo-yl benzoate (223677-27-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 96 percent / 1H-imidazole / dimethylformamide

2.1: BuLi / hexane; tetrahydrofuran / 0.5 h / -25 °C

2.2: 42 percent / tetrahydrofuran / 3 h / -60 - -20 °C

3.1: 8.24 g / 220 °C / 0.2 Torr

4.1: LDA / tetrahydrofuran / -78 °C

4.2: -78 - 20 °C

5.1: Et₂Zn / hexane; 1,2-dichloro-ethane / -20 - 20 °C

6.1: FeCl₃; pyridine / dimethylformamide / 60 °C

7.1: DBU; t-BuOOH / 2,2,4-trimethyl-pentane; CH₂Cl₂

8.1: NaBH₄ / methanol / 0 °C

9.1: pyridine

10.1: Bu₄NF / tetrahydrofuran

11.1: 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂

12.1: CF₃COOH / CH₂Cl₂ / 20 °C

13.1: DMAP / pyridine

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; diethylzinc; iron(III) chloride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 2.1: Johnson and Zeller method / 4.1: Saegusa method / 5.1: Simmons-Smith cyclopropanation / 11.1: Dess-Martin oxidation;

DOI:10.1002/1522-2675(20010613)84:6<1363::AID-HLCA1363>3.0.CO;2-M

Reference yield:

(+/-)-7-oxabicyclo<2.2.1>hept-5-en-2-one (88708-22-9,94482-73-2,94482-75-4,95530-78-2) → (1S,2S,3R,4R,5R,6S)-2-exo,4-endo-bis(acetyloxy)-6-endo-(benzyloxy)-7-oxo-8-oxabicyclo[3.2.1]oct-3-endo-yl benzoate (223677-27-8)

Guidance literature:

Multi-step reaction with 16 steps

1.1: TMSOTf

2.1: mCPBA / CHCl₃

3.1: HSO₃F / CH₂Cl₂

4.1: 96 percent / 1H-imidazole / dimethylformamide

5.1: BuLi / hexane; tetrahydrofuran / 0.5 h / -25 °C

5.2: 42 percent / tetrahydrofuran / 3 h / -60 - -20 °C

6.1: 8.24 g / 220 °C / 0.2 Torr

7.1: LDA / tetrahydrofuran / -78 °C

7.2: -78 - 20 °C

8.1: Et₂Zn / hexane; 1,2-dichloro-ethane / -20 - 20 °C

9.1: FeCl₃; pyridine / dimethylformamide / 60 °C

10.1: DBU; t-BuOOH / 2,2,4-trimethyl-pentane; CH₂Cl₂

11.1: NaBH₄ / methanol / 0 °C

12.1: pyridine

13.1: Bu₄NF / tetrahydrofuran

14.1: 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂

15.1: CF₃COOH / CH₂Cl₂ / 20 °C

16.1: DMAP / pyridine

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; diethylzinc; fluorosulphonic acid; iron(III) chloride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; chloroform; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 5.1: Johnson and Zeller method / 7.1: Saegusa method / 8.1: Simmons-Smith cyclopropanation / 14.1: Dess-Martin oxidation;

DOI:10.1002/1522-2675(20010613)84:6<1363::AID-HLCA1363>3.0.CO;2-M

Reference yield:

(1RS,4RS,5RS,6SR)-6-endo-(benzyloxy)-5-exo-{[(t-butyl)dimethylsilyl]oxy}-7-oxabicyclo[2.2.1]heptan-2-one (139391-31-4,139491-27-3) → (1S,2S,3R,4R,5R,6S)-2-exo,4-endo-bis(acetyloxy)-6-endo-(benzyloxy)-7-oxo-8-oxabicyclo[3.2.1]oct-3-endo-yl benzoate (223677-27-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: BuLi / hexane; tetrahydrofuran / 0.5 h / -25 °C

1.2: 42 percent / tetrahydrofuran / 3 h / -60 - -20 °C

2.1: 8.24 g / 220 °C / 0.2 Torr

3.1: LDA / tetrahydrofuran / -78 °C

3.2: -78 - 20 °C

4.1: Et₂Zn / hexane; 1,2-dichloro-ethane / -20 - 20 °C

5.1: FeCl₃; pyridine / dimethylformamide / 60 °C

6.1: DBU; t-BuOOH / 2,2,4-trimethyl-pentane; CH₂Cl₂

7.1: NaBH₄ / methanol / 0 °C

8.1: pyridine

9.1: Bu₄NF / tetrahydrofuran

10.1: 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂

11.1: CF₃COOH / CH₂Cl₂ / 20 °C

12.1: DMAP / pyridine

With pyridine; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; diethylzinc; iron(III) chloride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: Johnson and Zeller method / 3.1: Saegusa method / 4.1: Simmons-Smith cyclopropanation / 10.1: Dess-Martin oxidation;

DOI:10.1002/1522-2675(20010613)84:6<1363::AID-HLCA1363>3.0.CO;2-M

upstream raw materials:

acetic anhydride

(1S,2S,3R,4R,5R,6S)-6-endo-(benzyloxy)-2-exo,4-endo-dihydroxy-7-oxo-8-oxabicyclo[3.2.1]oct-3-endo-yl benzoate

(+/-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one

(+/-)-7-oxabicyclo<2.2.1>hept-5-en-2-one

Downstream raw materials:

(1R,2R,5S,6S,7R,8S)-6-exo,8-endo-bis(acetyloxy)-2-endo-(benzyloxy)-4-oxo-3,9-dioxabicyclo[3.3.1]non-7-endo-yl benzoate

methyl 3,5-di-O-acetyl-2,6-anhydro-4-O-benzoyl-D-glycero-D-galacto-hepturonate diethyl dithioacetal

methyl (7S)-3,5,7-tri-O-acetyl-7-C-[(1R,2S,3R,4S,5R,7S)-2-endo-(acetyloxy)-7-endo-(benzyloxy)-6-oxo-4-exo-(phenylthio)-8-oxabicyclo[3.2.1]oct-3-endo-yl]-2,6-anhydro-4-O-benzoyl-L-glycero-D-manno-heptonate

methyl (7S)-3,5-di-O-acetyl-2,6-anhydro-4-O-benzoyl-7-C-{(1R,2S,3R,4S,5R,6S,7R)-6-endo-(benzyloxy)-7-exo-{[(tert-butyl)dimethylsilyl]oxy}-4-endo-hydroxy-2-exo-(phenylthio)-8-oxabicyclo[3.2.1]oct-3-endo-yl}-L-glycero-D-manno-heptonate

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