(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

Base Information

• Chemical Name: (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
• CAS No.: 368445-78-7
• Molecular Formula: C₂₇H₃₄O₆Si
• Molecular Weight: 482.649

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 21 articles about (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 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,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,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)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; tert.-butylhydroperoxide; sodium tetrahydroborate; 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) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / methanol / 0 °C

2: pyridine

With sodium tetrahydroborate; In pyridine; methanol;

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,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)

Guidance literature:

Multi-step reaction with 3 steps

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

2: NaBH₄ / methanol / 0 °C

3: pyridine

With tert.-butylhydroperoxide; sodium tetrahydroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; 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:

benzoyl chloride

(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

(+/-)-(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:

(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

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

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