5-{(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1-triisopropylsilanyloxy-meth-(Z)-ylidene]-tetrahydro-furan-2-yl}-benzo[1,3]dioxole

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Chemical Name:5-{(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1-triisopropylsilanyloxy-meth-(Z)-ylidene]-tetrahydro-furan-2-yl}-benzo[1,3]dioxole
CAS No.:473433-20-4
Molecular Formula:C₃₈H₅₂O₅Si₂
Molecular Weight:644.999
Hs Code.:

Synonyms:5-{(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1-triisopropylsilanyloxy-meth-(Z)-ylidene]-tetrahydro-furan-2-yl}-benzo[1,3]dioxole

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Chemical Property of 5-{(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1-triisopropylsilanyloxy-meth-(Z)-ylidene]-tetrahydro-furan-2-yl}-benzo[1,3]dioxole

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Technology Process of 5-{(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1-triisopropylsilanyloxy-meth-(Z)-ylidene]-tetrahydro-furan-2-yl}-benzo[1,3]dioxole

There total 9 articles about 5-{(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1-triisopropylsilanyloxy-meth-(Z)-ylidene]-tetrahydro-furan-2-yl}-benzo[1,3]dioxole 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: 100.0%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 473433-18-0
(3R/S,4R,5S)-4-[(tert-butyldiphenylsilyloxy)methyl]-5-(3,4-methylenedioxyphenyl)tetrahydrofuran-3-carboxaldehyde

: 473433-20-4
5-{(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1-triisopropylsilanyloxy-meth-(Z)-ylidene]-tetrahydro-furan-2-yl}-benzo[1,3]dioxole

Guidance literature:: With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1271/bbb.66.1495

Reference yield:

: 195321-29-0
(1S,2R)-1-Benzo[1,3]dioxol-5-yl-2-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-en-1-ol

: 473433-20-4
5-{(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1-triisopropylsilanyloxy-meth-(Z)-ylidene]-tetrahydro-furan-2-yl}-benzo[1,3]dioxole

Guidance literature:: Multi-step reaction with 9 steps

1.1: 4-methylmorpholine N-oxide; osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol / 24 h / 20 °C

2.1: 5.24 g / sodium periodate / methanol / 3 h / 20 °C

3.1: 5.22 g / Ag₂CO₃-Celite / toluene / 1 h / Heating

4.1: LHMDS / tetrahydrofuran / 0.5 h / -75 °C

4.2: 3.04 g / tetrahydrofuran / 2 h / -75 °C

5.1: 22 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 20 °C

6.1: 57 percent / sodium borohydride / ethanol / 3 h / 20 °C

7.1: 83 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 24 h / 20 °C

8.1: 72 percent / pyridinium chlorochromate; MS 4A / CH₂Cl₂ / 5 h / 20 °C

9.1: 100 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

With dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; (1S)-10-camphorsulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1271/bbb.66.1495

Reference yield:

: 473433-21-5
(4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-ol

: 473433-20-4
5-{(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1-triisopropylsilanyloxy-meth-(Z)-ylidene]-tetrahydro-furan-2-yl}-benzo[1,3]dioxole

Guidance literature:: Multi-step reaction with 7 steps

1.1: 5.22 g / Ag₂CO₃-Celite / toluene / 1 h / Heating

2.1: LHMDS / tetrahydrofuran / 0.5 h / -75 °C

2.2: 3.04 g / tetrahydrofuran / 2 h / -75 °C

3.1: 22 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 20 °C

4.1: 57 percent / sodium borohydride / ethanol / 3 h / 20 °C

5.1: 83 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 24 h / 20 °C

6.1: 72 percent / pyridinium chlorochromate; MS 4A / CH₂Cl₂ / 5 h / 20 °C

7.1: 100 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

With dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; (1S)-10-camphorsulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; toluene;
DOI:10.1271/bbb.66.1495