(+)-(1R,3'R,4'S_.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-nitro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol

Base Information

• Chemical Name: (+)-(1R,3'R,4'S_.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-nitro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol
• CAS No.: 1308314-72-8
• Molecular Formula: C₃₉H₅₅NO₇Si₂
• Molecular Weight: 706.039

Synonyms:

Chemical Property of (+)-(1R,3'R,4'S_.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-nitro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1R,3'R,4'S_.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-nitro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol

There total 6 articles about (+)-(1R,3'R,4'S_.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-nitro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-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:

(2-bromo-5-nitro-phenyl)methanol (332883-48-4) → (+)-(1S,3'R,4'S.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-nitro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol (1308314-95-5) + (+)-(1R,3'R,4'S.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-nitro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol (1308314-72-8)

Guidance literature:

Multi-step reaction with 5 steps

1: dmap; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / Reflux; Darkness; Inert atmosphere

3: methanol; potassium carbonate / tetrahydrofuran

4: 3,3-dimethyldioxirane / methanol; dichloromethane; acetone / 0.17 h / -78 °C / Inert atmosphere

5: dichloromethane; acetone / -78 - 20 °C / Inert atmosphere

With methanol; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 3,3-dimethyldioxirane; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; 2: Stille coupling;

DOI:10.1021/ja201249c

Reference yield:

2-bromo-5-nitrobenzyl acetate (1255719-57-3) → (+)-(1S,3'R,4'S.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-nitro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol (1308314-95-5) + (+)-(1R,3'R,4'S.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-nitro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol (1308314-72-8)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / Reflux; Darkness; Inert atmosphere

2: methanol; potassium carbonate / tetrahydrofuran

3: 3,3-dimethyldioxirane / methanol; dichloromethane; acetone / 0.17 h / -78 °C / Inert atmosphere

4: dichloromethane; acetone / -78 - 20 °C / Inert atmosphere

With methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 3,3-dimethyldioxirane; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; 1: Stille coupling;

DOI:10.1021/ja201249c

Reference yield:

(-)-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)-5-nitrophenyl)methanol (1308314-44-4) → (+)-(1S,3'R,4'S.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-nitro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol (1308314-95-5) + (+)-(1R,3'R,4'S.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-nitro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol (1308314-72-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 3,3-dimethyldioxirane / methanol; dichloromethane; acetone / 0.17 h / -78 °C / Inert atmosphere

2: dichloromethane; acetone / -78 - 20 °C / Inert atmosphere

With 3,3-dimethyldioxirane; In methanol; dichloromethane; acetone;

DOI:10.1021/ja201249c

upstream raw materials:

(2-bromo-5-nitro-phenyl)methanol

2-bromo-5-nitrobenzyl acetate

(-)-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)-5-nitrophenyl)methanol

2-bromo-5-nitrobenzoic acid

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