(1R,2S,4R,5S,6S,7R,8R)-7-endo-(benzyloxy)-8-exo-hydroxy-3,9-dioxatricyclo[4.2.1.0^2,4]non-5-endo-yl benzoate

Base Information

• Chemical Name: (1R,2S,4R,5S,6S,7R,8R)-7-endo-(benzyloxy)-8-exo-hydroxy-3,9-dioxatricyclo[4.2.1.0^2,4]non-5-endo-yl benzoate
• CAS No.: 223677-25-6
• Molecular Formula: C₂₁H₂₀O₆
• Molecular Weight: 368.386

Synonyms:(1R,2S,4R,5S,6S,7R,8R)-7-endo-(benzyloxy)-8-exo-hydroxy-3,9-dioxatricyclo[4.2.1.0^2,4]non-5-endo-yl benzoate

Chemical Property of (1R,2S,4R,5S,6S,7R,8R)-7-endo-(benzyloxy)-8-exo-hydroxy-3,9-dioxatricyclo[4.2.1.0^2,4]non-5-endo-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,4R,5S,6S,7R,8R)-7-endo-(benzyloxy)-8-exo-hydroxy-3,9-dioxatricyclo[4.2.1.0^2,4]non-5-endo-yl benzoate

There total 20 articles about (1R,2S,4R,5S,6S,7R,8R)-7-endo-(benzyloxy)-8-exo-hydroxy-3,9-dioxatricyclo[4.2.1.0^2,4]non-5-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:

(1S,2S,4R,5R,6S,7S,8R)-7-endo-(benzyloxy)-8-exo-{[(tert-butyl)dimethylsilyl]oxy}-3,9-dioxatricyclo[4.2.1.02,4]non-5-endo-yl benzoate (368445-78-7) → (1R,2S,4R,5S,6S,7R,8R)-7-endo-(benzyloxy)-8-exo-hydroxy-3,9-dioxatricyclo[4.2.1.02,4]non-5-endo-yl benzoate (223677-25-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; water; at 0 ℃; for 3.5h; Yield given;

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

Reference yield:

(1S,4S,5S,6R)-6-endo-(benzyloxy)-5-exo-<<(t-butyl)dimethylsilyl>oxy>-7-oxabicyclo<2.2.1>heptan-2-one (139391-31-4) → (1R,2S,4R,5S,6S,7R,8R)-7-endo-(benzyloxy)-8-exo-hydroxy-3,9-dioxatricyclo[4.2.1.02,4]non-5-endo-yl benzoate (223677-25-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LDA / tetrahydrofuran / -78 °C

1.2: -78 - 20 °C

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

3.1: FeCl₃; pyridine / dimethylformamide / 60 °C

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

5.1: NaBH₄ / methanol / 0 °C

6.1: pyridine

7.1: Bu₄NF / tetrahydrofuran

With pyridine; tert.-butylhydroperoxide; sodium tetrahydroborate; tetrabutyl ammonium fluoride; diethylzinc; iron(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: Saegusa method / 2.1: Simmons-Smith cyclopropanation;

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

Reference yield:

(1S,2R,4R,6S,7S,8R)-7-endo-(benzyloxy)-8-exo-{[(tert-butyl)dimethylsilyl]oxy}-3,9-dioxatricyclo[4.2.1.02,4]nonan-5-one (368445-79-8) → (1R,2S,4R,5S,6S,7R,8R)-7-endo-(benzyloxy)-8-exo-hydroxy-3,9-dioxatricyclo[4.2.1.02,4]non-5-endo-yl benzoate (223677-25-6)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / methanol / 0 °C

2: pyridine

3: Bu₄NF / tetrahydrofuran

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine; methanol;

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

upstream raw materials:

(1S,2S,4R,5R,6S,7S,8R)-7-endo-(benzyloxy)-8-exo-{[(tert-butyl)dimethylsilyl]oxy}-3,9-dioxatricyclo[4.2.1.0^2,4]non-5-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

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

Downstream raw materials:

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

(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 (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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