(-)-(1R,3'S,4'R,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isochroman-1,2'-pyran]-3'-ol

Base Information

Chemical Name:(-)-(1R,3'S,4'R,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isochroman-1,2'-pyran]-3'-ol
CAS No.:1177259-12-9
Molecular Formula:C₄₀H₅₈O₅Si₂
Molecular Weight:675.069
Hs Code.:

Synonyms:(-)-(1R,3'S,4'R,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isochroman-1,2'-pyran]-3'-ol

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Chemical Property of (-)-(1R,3'S,4'R,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isochroman-1,2'-pyran]-3'-ol

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Technology Process of (-)-(1R,3'S,4'R,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isochroman-1,2'-pyran]-3'-ol

There total 10 articles about (-)-(1R,3'S,4'R,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[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: 96.0%

: 1177258-89-7
(+)-2-(2-((2R,4R)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)phenyl)ethanol

: 1177259-12-9
(-)-(1R,3'S,4'R,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isochroman-1,2'-pyran]-3'-ol

Guidance literature:: (+)-2-(2-((2R,4R)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)phenyl)ethanol; With 3,3-dimethyldioxirane; In dichloromethane; acetone; at -78 ℃; for 0.166667h; Inert atmosphere;

With titanium(IV) isopropylate; In dichloromethane; acetone; at -78 - 0 ℃; optical yield given as %de; stereoselective reaction; Inert atmosphere;
DOI:10.1021/ol901437f

Reference yield:

: 1177258-89-7
(+)-2-(2-((2R,4R)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)phenyl)ethanol

: 1177259-29-8
(1S,3'S,4'R,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isochroman-1,2'-pyran]-3'-ol

: 1177259-12-9
(-)-(1R,3'S,4'R,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isochroman-1,2'-pyran]-3'-ol

Guidance literature:: With 3,3-dimethyldioxirane; acetic acid; In dichloromethane; acetone; at -63 - -44 ℃; optical yield given as %de; stereoselective reaction;
DOI:10.1021/ol901437f

Reference yield:

: 858855-88-6
2-bromophenethyl acetate

: 1177259-12-9
(-)-(1R,3'S,4'R,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isochroman-1,2'-pyran]-3'-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 6 h / 110 °C / Inert atmosphere; Darkness

2.1: methanol; potassium carbonate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

3.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 0.17 h / -78 °C / Inert atmosphere

3.2: -78 - 0 °C / Inert atmosphere

With methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 3,3-dimethyldioxirane; potassium carbonate; In tetrahydrofuran; dichloromethane; acetone; toluene; 1.1: Stille coupling;
DOI:10.1021/ol901437f