(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

Base Information

• Chemical Name: (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
• CAS No.: 223677-29-0
• Molecular Formula: C₂₅H₂₄O₁₀
• Molecular Weight: 484.46

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 18 articles about (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 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: 84.0%

(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) → (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 (223677-29-0)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃;

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

Reference yield: 83.0%

Acetic acid (1R,2S,3R,4S,5S,7S)-4-acetoxy-3-benzoyl-7-benzyloxy-6-oxo-8-oxa-bicyclo[3.2.1]oct-2-yl ester → (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 (223677-29-0)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid;

DOI:10.1016/S0040-4039(99)00432-3

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) → (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 (223677-29-0)

Guidance literature:

Multi-step reaction with 14 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

14.1: 84 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 20 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; diethylzinc; iron(III) chloride; sodium hydrogencarbonate; 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; 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 / 14.1: Baeyer-Villiger oxidation;

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

upstream raw materials:

(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

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

(1S,4S,5S,6R)-6-endo-(benzyloxy)-5-exo-<<(t-butyl)dimethylsilyl>oxy>-7-oxabicyclo<2.2.1>heptan-2-one

(1RS,4RS,5RS,6SR)-6-endo-(benzyloxy)-5-exo-{[(t-butyl)dimethylsilyl]oxy}-7-oxabicyclo[2.2.1]heptan-2-one

Downstream raw materials:

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

(2S,3S,4R,5R,6S)-3,5-Diacetoxy-4-benzoyloxy-6-{(S)-[(1R,2S,3R,5S,6S,7R)-6-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-4-oxo-2-phenylsulfanyl-8-oxa-bicyclo[3.2.1]oct-3-yl]-hydroxy-methyl}-tetrahydro-pyran-2-carboxylic acid methyl ester

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

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