(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
• Mol file: 473433-18-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

(2S,3R,4R/S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran (473433-17-9) → (3R/S,4R,5S)-4-[(tert-butyldiphenylsilyloxy)methyl]-5-(3,4-methylenedioxyphenyl)tetrahydrofuran-3-carboxaldehyde (473433-18-0)

Guidance literature:

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

DOI:10.1271/bbb.66.1495

Reference yield:

(1S,2R)-1-Benzo[1,3]dioxol-5-yl-2-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-en-1-ol (195321-29-0) → (3R/S,4R,5S)-4-[(tert-butyldiphenylsilyloxy)methyl]-5-(3,4-methylenedioxyphenyl)tetrahydrofuran-3-carboxaldehyde (473433-18-0)

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:

(3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-(3,4-methylenedioxyphenyl)-4-butanolide (473433-14-6) → (3R/S,4R,5S)-4-[(tert-butyldiphenylsilyloxy)methyl]-5-(3,4-methylenedioxyphenyl)tetrahydrofuran-3-carboxaldehyde (473433-18-0)

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

upstream raw materials:

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

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

(3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-(3,4-methylenedioxyphenyl)-4-butanolide

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

Downstream raw materials:

(3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-furan-3-carbaldehyde

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