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

Base Information

• Chemical Name: (3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-furan-3-carbaldehyde
• CAS No.: 189557-98-0
• Molecular Formula: C₂₉H₃₂O₆Si
• Molecular Weight: 504.655
• Mol file: 189557-98-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 18 articles about (3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-furan-3-carbaldehyde 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: 83.0%

(3R,4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-tetrahydro-furan-3-ol (189557-95-7) → (3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-furan-3-carbaldehyde (189557-98-0)

Guidance literature:

With pyridine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dimethyl sulfoxide; benzene; for 20h; Ambient temperature;

DOI:10.1271/bbb.61.743

Reference yield: 71.0%

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) → (3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-furan-3-carbaldehyde (189557-98-0)

Guidance literature:

5-{(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[1-triisopropylsilanyloxy-meth-(Z)-ylidene]-tetrahydro-furan-2-yl}-benzo[1,3]dioxole; With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 20 ℃; for 24h;

With N,N`-dimethylethylenediamine; In benzene; for 0.5h; Heating;

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) → (3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-furan-3-carbaldehyde (189557-98-0)

Guidance literature:

Multi-step reaction with 10 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

10.1: 4-methylmorpholine N-oxide; osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol / 24 h / 20 °C

10.2: 71 percent / N,N'-dimethylethylenediamine / benzene / 0.5 h / Heating

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

upstream raw materials:

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

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

(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

Downstream raw materials:

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