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

Base Information

Chemical Name:(3R/S,4R,5S)-4-[(tert-butyldiphenylsilyloxy)methyl]-5-(3,4-methylenedioxyphenyl)tetrahydrofuran-3-carboxaldehyde
CAS No.:473433-18-0
Molecular Formula:C₂₉H₃₂O₅Si
Molecular Weight:488.656
Hs Code.:

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

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Chemical Property of (3R/S,4R,5S)-4-[(tert-butyldiphenylsilyloxy)methyl]-5-(3,4-methylenedioxyphenyl)tetrahydrofuran-3-carboxaldehyde

Chemical Property:

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Technology Process of (3R/S,4R,5S)-4-[(tert-butyldiphenylsilyloxy)methyl]-5-(3,4-methylenedioxyphenyl)tetrahydrofuran-3-carboxaldehyde

There total 8 articles about (3R/S,4R,5S)-4-[(tert-butyldiphenylsilyloxy)methyl]-5-(3,4-methylenedioxyphenyl)tetrahydrofuran-3-carboxaldehyde 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: 72.0%

: 473433-17-9
(2S,3R,4R/S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

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

Guidance literature:: With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 5h;
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

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

Guidance literature:: Multi-step reaction with 8 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

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; (1S)-10-camphorsulfonic acid; 4-methylmorpholine N-oxide; 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:

: 473433-14-6
(3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-(3,4-methylenedioxyphenyl)-4-butanolide

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

Guidance literature:: Multi-step reaction with 5 steps

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

1.2: 3.04 g / tetrahydrofuran / 2 h / -75 °C

2.1: 22 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 20 °C

3.1: 57 percent / sodium borohydride / ethanol / 3 h / 20 °C

4.1: 83 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 24 h / 20 °C

5.1: 72 percent / pyridinium chlorochromate; MS 4A / CH₂Cl₂ / 5 h / 20 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; (1S)-10-camphorsulfonic acid; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1271/bbb.66.1495