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

Base Information

• Chemical Name: (1S,2R,4R,6S,7S,8R)-7-endo-(benzyloxy)-8-exo-{[(tert-butyl)dimethylsilyl]oxy}-3,9-dioxatricyclo[4.2.1.0^2,4]nonan-5-one
• CAS No.: 368445-79-8
• Molecular Formula: C₂₀H₂₈O₅Si
• Molecular Weight: 376.525

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about (1S,2R,4R,6S,7S,8R)-7-endo-(benzyloxy)-8-exo-{[(tert-butyl)dimethylsilyl]oxy}-3,9-dioxatricyclo[4.2.1.0^2,4]nonan-5-one 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:

(-)-6-exo-<(tert-butyl)dimethylsilyloxy>-7-endo-benzyloxy-8-oxabicyclo<3.2.1>oct-3-en-2-one (223677-23-4) → (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)

Guidance literature:

With tert.-butylhydroperoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 3h;

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) → (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)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; tert.-butylhydroperoxide; diethylzinc; iron(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; 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,4S,5S,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-triethylsilanyloxy-7-oxa-bicyclo[2.2.1]hept-2-ene → (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)

Guidance literature:

Multi-step reaction with 3 steps

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

2: FeCl₃; pyridine / dimethylformamide / 60 °C

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

With pyridine; tert.-butylhydroperoxide; diethylzinc; iron(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 2,2,4-trimethylpentane; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: Simmons-Smith cyclopropanation;

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

upstream raw materials:

(-)-6-exo-<(tert-butyl)dimethylsilyloxy>-7-endo-benzyloxy-8-oxabicyclo<3.2.1>oct-3-en-2-one

(+/-)-(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:

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

(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

(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

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

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