(+)-(1R,4R,5S,6S,7R)-4-exo-{[(4-bromophenyl)sulfonyl]oxy}-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}-7-endo-(methoxymethoxy)-2,7-dioxabicyclo[3.2.1]...

Base Information

• Chemical Name: (+)-(1R,4R,5S,6S,7R)-4-exo-{[(4-bromophenyl)sulfonyl]oxy}-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}-7-endo-(methoxymethoxy)-2,7-dioxabicyclo[3.2.1]...
• CAS No.: 248243-27-8
• Molecular Formula: C₂₉H₄₀BrNO₁₃SSi
• Molecular Weight: 750.691

Synonyms:

Chemical Property of (+)-(1R,4R,5S,6S,7R)-4-exo-{[(4-bromophenyl)sulfonyl]oxy}-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}-7-endo-(methoxymethoxy)-2,7-dioxabicyclo[3.2.1]...

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1R,4R,5S,6S,7R)-4-exo-{[(4-bromophenyl)sulfonyl]oxy}-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}-7-endo-(methoxymethoxy)-2,7-dioxabicyclo[3.2.1]...

There total 1 articles about (+)-(1R,4R,5S,6S,7R)-4-exo-{[(4-bromophenyl)sulfonyl]oxy}-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}-7-endo-(methoxymethoxy)-2,7-dioxabicyclo[3.2.1]... 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:

(+)-(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 (248243-26-7) → (+)-(1R,4R,5S,6S,7R)-4-exo-{[(4-bromophenyl)sulfonyl]oxy}-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}-7-endo-(methoxymethoxy)-2,7-dioxabicyclo[3.2.1]... (248243-27-8)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 25 ℃; for 20h;

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

Reference yield:

(+)-(1R,4R,5S,6S,7R)-4-exo-{[(4-bromophenyl)sulfonyl]oxy}-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}-7-endo-(methoxymethoxy)-2,7-dioxabicyclo[3.2.1]... (248243-27-8) → 1,4-anhydro-3-[(6S)-5-{[(benzyloxy)carbonyl]amino}-5-deoxy-1,2-O-isopropylidene-β-L-idofuranos-6C-yl]-3-deoxy-2,6-bis-O-(methoxymethyl)-α-D-galactopyranose (248243-32-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / K₂CO₃ / dimethylformamide / 2 h / 0 - 25 °C

2: LiAlH₄ / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

3: 212 mg / (i-Pr)2NEt / CH₂Cl₂ / 16 h / 0 - 25 °C

4: LiAlH / diethyl ether / 120 h / 25 °C

5: 180 mg / NaHCO₃ / aq. ethanol / 1.5 h / 25 °C

With lithium aluminium tetrahydride; sodium hydrogencarbonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Ring cleavage / 2: Reduction / 3: Substitution / 4: Reduction / 5: Substitution;

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

upstream raw materials:

(+)-(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

Downstream raw materials:

1,4-anhydro-3-[(6S)-5-{[(benzyloxy)carbonyl]amino}-5-deoxy-1,2-O-isopropylidene-β-L-idofuranos-6C-yl]-3-deoxy-2,6-bis-O-(methoxymethyl)-α-D-galactopyranose

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