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

Base Information

Chemical Name:(+)-(1S,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-3H-spiro[benzo[c]oxepine-1,2'-pyran]-3'-ol
CAS No.:1177259-04-9
Molecular Formula:C₄₁H₆₀O₅Si₂
Molecular Weight:689.095
Hs Code.:

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

There total 11 articles about (+)-(1S,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-3H-spiro[benzo[c]oxepine-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: 90.0%

: 1177258-87-5
(-)-3-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)phenyl)propan-1-ol

: 1177259-04-9
(+)-(1S,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-3H-spiro[benzo[c]oxepine-1,2'-pyran]-3'-ol

Guidance literature:: (-)-3-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)phenyl)propan-1-ol; 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:

: 67-56-1
methanol

: 1177258-87-5
(-)-3-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)phenyl)propan-1-ol

: 1177259-04-9
(+)-(1S,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-3H-spiro[benzo[c]oxepine-1,2'-pyran]-3'-ol

: C₄₂H₆₄O₆Si₂

Guidance literature:: With 3,3-dimethyldioxirane; In dichloromethane; acetone; at -63 ℃; for 3h;
DOI:10.1021/ol901437f

Reference yield:

: C₄₃H₆₂O₅Si₂

: 1177259-04-9
(+)-(1S,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-3H-spiro[benzo[c]oxepine-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