(+)-(1S,3'R,4'S_.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-chloro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydrospiro[isochroman-1,2'-pyran]-3'-ol

Base Information

• Chemical Name: (+)-(1S,3'R,4'S_.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-chloro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydrospiro[isochroman-1,2'-pyran]-3'-ol
• CAS No.: 1308314-90-0
• Molecular Formula: C₄₀H₅₇ClO₅Si₂
• Molecular Weight: 709.514

Synonyms:

Chemical Property of (+)-(1S,3'R,4'S_.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-chloro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydrospiro[isochroman-1,2'-pyran]-3'-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (+)-(1S,3'R,4'S_.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-chloro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydrospiro[isochroman-1,2'-pyran]-3'-ol

There total 10 articles about (+)-(1S,3'R,4'S_.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-chloro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydrospiro[isochroman-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:

C41H59ClO4Si2 → (+)-(1S,3'R,4'S.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-chloro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydrospiro[isochroman-1,2'-pyran]-3'-ol (1308314-90-0) + (+)-(1R,3'R,4'S.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-chloro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydrospiro[isochroman-1,2'-pyran]-3'-ol (1308314-66-0)

Guidance literature:

In dichloromethane; acetone; at -78 - 20 ℃; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ja201249c

Reference yield:

2-bromo-5-chlorobenzaldehyde (174265-12-4) → (+)-(1S,3'R,4'S.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-chloro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydrospiro[isochroman-1,2'-pyran]-3'-ol (1308314-90-0) + (+)-(1R,3'R,4'S.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-chloro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydrospiro[isochroman-1,2'-pyran]-3'-ol (1308314-66-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium hexamethylsilazane / toluene / 1 h / 0 - 20 °C / Inert atmosphere

1.2: 7 h / 0 - 20 °C / Inert atmosphere

2.1: hydrogenchloride / tetrahydrofuran; water / 12 h / Reflux

3.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere

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

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

6.1: methanol; potassium carbonate / tetrahydrofuran

7.1: 3,3-dimethyldioxirane / methanol; dichloromethane; acetone / 0.17 h / -78 °C / Inert atmosphere

8.1: methanol / dichloromethane; acetone / -63 - 20 °C / Inert atmosphere

With hydrogenchloride; methanol; dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 3,3-dimethyldioxirane; potassium hexamethylsilazane; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 5.1: Stille coupling;

DOI:10.1021/ja201249c

Reference yield:

C42H59ClO5Si2 → (+)-(1S,3'R,4'S.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-chloro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydrospiro[isochroman-1,2'-pyran]-3'-ol (1308314-90-0) + (+)-(1R,3'R,4'S.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-chloro-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydrospiro[isochroman-1,2'-pyran]-3'-ol (1308314-66-0)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol; potassium carbonate / tetrahydrofuran

2: 3,3-dimethyldioxirane / methanol; dichloromethane; acetone / 0.17 h / -78 °C / Inert atmosphere

3: methanol / dichloromethane; acetone / -63 - 20 °C / Inert atmosphere

With methanol; 3,3-dimethyldioxirane; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1021/ja201249c

upstream raw materials:

2-bromo-5-chlorobenzaldehyde

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

(2-bromo-5-chlorophenyl)acetaldehyde

2-(2-bromo-5-chloro-phenyl)ethanol

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