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

Base Information

• Chemical Name: (1S,2S,4S,5R,6R,7S,8R)-7-endo-(benzyloxy)-8-exo-{[(tert-butyl)dimethylsilyl]oxy}-3,9-dioxatricyclo[4.2.1.0^2,4]nonan-5-endo-ol
• CAS No.: 368445-80-1
• Molecular Formula: C₂₀H₃₀O₅Si
• Molecular Weight: 378.541

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

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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 20 articles about (1S,2S,4S,5R,6R,7S,8R)-7-endo-(benzyloxy)-8-exo-{[(tert-butyl)dimethylsilyl]oxy}-3,9-dioxatricyclo[4.2.1.0^2,4]nonan-5-endo-ol 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,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) → (1S,2S,4S,5R,6R,7S,8R)-7-endo-(benzyloxy)-8-exo-{[(tert-butyl)dimethylsilyl]oxy}-3,9-dioxatricyclo[4.2.1.02,4]nonan-5-endo-ol (368445-80-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

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,2S,4S,5R,6R,7S,8R)-7-endo-(benzyloxy)-8-exo-{[(tert-butyl)dimethylsilyl]oxy}-3,9-dioxatricyclo[4.2.1.02,4]nonan-5-endo-ol (368445-80-1)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; tert.-butylhydroperoxide; sodium tetrahydroborate; diethylzinc; iron(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; 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:

(-)-6-exo-<(tert-butyl)dimethylsilyloxy>-7-endo-benzyloxy-8-oxabicyclo<3.2.1>oct-3-en-2-one (223677-23-4) → (1S,2S,4S,5R,6R,7S,8R)-7-endo-(benzyloxy)-8-exo-{[(tert-butyl)dimethylsilyl]oxy}-3,9-dioxatricyclo[4.2.1.02,4]nonan-5-endo-ol (368445-80-1)

Guidance literature:

Multi-step reaction with 2 steps

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

2: NaBH₄ / methanol / 0 °C

With tert.-butylhydroperoxide; sodium tetrahydroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; 2,2,4-trimethylpentane; dichloromethane;

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

upstream raw materials:

(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

(+/-)-(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,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

(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

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

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