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

Base Information

Chemical Name:(+)-(1S,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol
CAS No.:1177259-02-7
Molecular Formula:C₃₉H₅₆O₅Si₂
Molecular Weight:661.042
Hs Code.:

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

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

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

There total 12 articles about (+)-(1S,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-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: 81.0%

: 1177258-85-3
(-)-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)phenyl)methanol

: 1177259-02-7
(+)-(1S,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol

Guidance literature:: (-)-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)phenyl)methanol; 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:

: 1177258-85-3
(-)-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)phenyl)methanol

: 1177259-02-7
(+)-(1S,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol

: 1177259-20-9
(+)-(1R,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol

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

Reference yield:

: C₄₁H₅₈O₅Si₂

: 1177259-02-7
(+)-(1S,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3'-ol

Guidance literature:: Multi-step reaction with 2 steps

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

2.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 0.17 h / -78 °C / Inert atmosphere

2.2: -78 - 0 °C / Inert atmosphere

With methanol; 3,3-dimethyldioxirane; potassium carbonate; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1021/ol901437f