(-)-(1R,2R,4S,5R,6R)-6-exo-{(R)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-5-endo-(methoxymethoxy)-3-oxo-7-oxabicyclo[2.2.1]hept-2-exo-yl 4-bromobenzenesulfonate

Base Information

• Chemical Name: (-)-(1R,2R,4S,5R,6R)-6-exo-{(R)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-5-endo-(methoxymethoxy)-3-oxo-7-oxabicyclo[2.2.1]hept-2-exo-yl 4-bromobenzenesulfonate
• CAS No.: 263405-51-2
• Molecular Formula: C₂₉H₄₀BrNO₁₂SSi
• Molecular Weight: 734.692

Synonyms:(-)-(1R,2R,4S,5R,6R)-6-exo-{(R)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-5-endo-(methoxymethoxy)-3-oxo-7-oxabicyclo[2.2.1]hept-2-exo-yl 4-bromobenzenesulfonate

Chemical Property of (-)-(1R,2R,4S,5R,6R)-6-exo-{(R)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-5-endo-(methoxymethoxy)-3-oxo-7-oxabicyclo[2.2.1]hept-2-exo-yl 4-bromobenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (-)-(1R,2R,4S,5R,6R)-6-exo-{(R)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-5-endo-(methoxymethoxy)-3-oxo-7-oxabicyclo[2.2.1]hept-2-exo-yl 4-bromobenzenesulfonate

There total 9 articles about (-)-(1R,2R,4S,5R,6R)-6-exo-{(R)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-5-endo-(methoxymethoxy)-3-oxo-7-oxabicyclo[2.2.1]hept-2-exo-yl 4-bromobenzenesulfonate 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:

4-bromobenzenesulfonyl chloride (98-58-8) + (1S,3R,4R,5S,6R)-5-[(R)-(tert-Butyl-dimethyl-silanyloxy)-((3aS,4aS,7aS,7bR)-6,6-dimethyl-3a,4a,7a,7b-tetrahydro-[1,3]dioxolo[4',5':4,5]furo[2,3-d]isoxazol-3-yl)-methyl]-3-hydroxy-6-methoxymethoxy-7-oxa-bicyclo[2.2.1]heptan-2-one → (-)-(1R,2R,4S,5R,6R)-6-exo-{(R)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-5-endo-(methoxymethoxy)-3-oxo-7-oxabicyclo[2.2.1]hept-2-exo-yl 4-bromobenzenesulfonate (263405-51-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 25 ℃; for 3h;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<193::AID-HLCA193>3.0.CO;2-I

Reference yield:

(-)-(3aS,5S,6S,6aR)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole-3-carbaldehyde (223138-07-6) → (-)-(1R,2R,4S,5R,6R)-6-exo-{(R)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-5-endo-(methoxymethoxy)-3-oxo-7-oxabicyclo[2.2.1]hept-2-exo-yl 4-bromobenzenesulfonate (263405-51-2)

Guidance literature:

Multi-step reaction with 7 steps

1: BuLi; Me₃SiNHSiMe₃ / tetrahydrofuran; hexane / 3 h / -78 °C

2: 93 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 25 °C

3: 90 percent / NaBH₄ / methanol / 0 °C

4: 94 percent / EtN(i-Pr)2 / CH₂Cl₂ / 21 h / 0 - 25 °C

5: 92 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 16 h / -78 - 25 °C

6: OsO₄; NaHCO₃; Me₃NO*2H₂O / CCl₄; tetrahydrofuran; H₂O / 2 h / 25 °C

7: Et₃N / CH₂Cl₂ / 3 h / 0 - 25 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; trimethylamine-N-oxide; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water; 1: Addition / 2: silylation / 3: Reduction / 4: Substitution / 5: Elimination / 6: double hydroxylation / 7: Acylation;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<193::AID-HLCA193>3.0.CO;2-I

Reference yield:

(-)-(1S,4R,5R,6R)-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-one (128573-16-0) → (-)-(1R,2R,4S,5R,6R)-6-exo-{(R)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-5-endo-(methoxymethoxy)-3-oxo-7-oxabicyclo[2.2.1]hept-2-exo-yl 4-bromobenzenesulfonate (263405-51-2)

Guidance literature:

Multi-step reaction with 7 steps

1: BuLi; Me₃SiNHSiMe₃ / tetrahydrofuran; hexane / 3 h / -78 °C

2: 93 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 25 °C

3: 90 percent / NaBH₄ / methanol / 0 °C

4: 94 percent / EtN(i-Pr)2 / CH₂Cl₂ / 21 h / 0 - 25 °C

5: 92 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 16 h / -78 - 25 °C

6: OsO₄; NaHCO₃; Me₃NO*2H₂O / CCl₄; tetrahydrofuran; H₂O / 2 h / 25 °C

7: Et₃N / CH₂Cl₂ / 3 h / 0 - 25 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; trimethylamine-N-oxide; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water; 1: Addition / 2: silylation / 3: Reduction / 4: Substitution / 5: Elimination / 6: double hydroxylation / 7: Acylation;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<193::AID-HLCA193>3.0.CO;2-I

upstream raw materials:

4-bromobenzenesulfonyl chloride

(-)-(1S,4R,5R,6R)-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-one

(-)-(3aS,5S,6S,6aR)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole-3-carbaldehyde

(-)-(1S,3S,4R,5R,6R)-6-endo-chloro-3-exo-{(R)-hydroxy[(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-one

Downstream raw materials:

(+)-(1R,4R,5S,6S,7R)-4-exo-{[(4-bromophenyl)sulfonyl]oxy}-6-exo-{(R)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-7-endo-(methoxymethoxy)-2,7-dioxabicyclo[3.2.1]...

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