(+)-(1R,2R,4S,5R,6R)-6-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-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-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-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.:248243-26-7
Molecular Formula:C₂₉H₄₀BrNO₁₂SSi
Molecular Weight:734.692
Hs Code.:

(+)-(1R,2R,4S,5R,6R)-6-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-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

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Chemical Property of (+)-(1R,2R,4S,5R,6R)-6-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-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

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Technology Process of (+)-(1R,2R,4S,5R,6R)-6-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-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 10 articles about (+)-(1R,2R,4S,5R,6R)-6-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-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:

: 98-58-8
4-bromobenzenesulfonyl chloride

: (1S,3R,4R,5S,6R)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((3aR,4aR,7aR,7bS)-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

: 248243-26-7
(+)-(1R,2R,4S,5R,6R)-6-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-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

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:

: 223421-32-7
(+)-(3aR,5R,6R,6aS)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole-3-carbaldehyde

: 248243-26-7
(+)-(1R,2R,4S,5R,6R)-6-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-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

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / BuLi; Me₃SiNHSiMe₃ / tetrahydrofuran; hexane / 3 h / -78 °C

2: 92 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 25 °C

3: 91 percent / NaBH₄ / methanol / 0 °C

4: 86 percent / EtN(i-Pr)2 / CH₂Cl₂ / 21 h / 0 - 25 °C

5: 95 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 16 h / -78 - 25 °C

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

7: 672 mg / 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:

: 69739-34-0
t-butyldimethylsiyl triflate

: 248243-26-7
(+)-(1R,2R,4S,5R,6R)-6-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-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

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 25 °C

2: 91 percent / NaBH₄ / methanol / 0 °C

3: 86 percent / EtN(i-Pr)2 / CH₂Cl₂ / 21 h / 0 - 25 °C

4: 95 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 16 h / -78 - 25 °C

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

6: 672 mg / Et₃N / CH₂Cl₂ / 3 h / 0 - 25 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; osmium(VIII) oxide; trimethylamine-N-oxide; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; 1: silylation / 2: Reduction / 3: Substitution / 4: Elimination / 5: double hydroxylation / 6: Acylation;
DOI:10.1002/(SICI)1522-2675(20000119)83:1<193::AID-HLCA193>3.0.CO;2-I