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

Base Information

• Chemical Name: (4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-ol
• CAS No.: 473433-21-5
• Molecular Formula: C₂₈H₃₂O₅Si
• Molecular Weight: 476.645
• Mol file: 473433-21-5.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-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:

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

Guidance literature:

With sodium periodate; In methanol; at 20 ℃; for 3h;

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

Guidance literature:

Multi-step reaction with 2 steps

1: 4-methylmorpholine N-oxide; osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol / 24 h / 20 °C

2: 5.24 g / sodium periodate / methanol / 3 h / 20 °C

With sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In methanol; water; acetone; tert-butyl alcohol;

DOI:10.1271/bbb.66.1495

Reference yield:

(4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-ol (473433-21-5) → 5-{(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1-triisopropylsilanyloxy-meth-(Z)-ylidene]-tetrahydro-furan-2-yl}-benzo[1,3]dioxole (473433-20-4)

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

upstream raw materials:

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

Downstream raw materials:

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

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

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

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

Refernces