(3aS,4R,6aR)-tetrahydro-4-([(tert-butyl)dimethylsilyloxy]methyl)-2,2-dimethylselenopheno[3,4-d][1,3]dioxole

Base Information

• Chemical Name: (3aS,4R,6aR)-tetrahydro-4-([(tert-butyl)dimethylsilyloxy]methyl)-2,2-dimethylselenopheno[3,4-d][1,3]dioxole
• CAS No.: 1006032-30-9
• Molecular Formula: C₂₄H₃₂O₃SeSi
• Molecular Weight: 475.562
• Mol file: 1006032-30-9.mol

Synonyms:(3aS,4R,6aR)-tetrahydro-4-([(tert-butyl)dimethylsilyloxy]methyl)-2,2-dimethylselenopheno[3,4-d][1,3]dioxole

Chemical Property of (3aS,4R,6aR)-tetrahydro-4-([(tert-butyl)dimethylsilyloxy]methyl)-2,2-dimethylselenopheno[3,4-d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4R,6aR)-tetrahydro-4-([(tert-butyl)dimethylsilyloxy]methyl)-2,2-dimethylselenopheno[3,4-d][1,3]dioxole

There total 16 articles about (3aS,4R,6aR)-tetrahydro-4-([(tert-butyl)dimethylsilyloxy]methyl)-2,2-dimethylselenopheno[3,4-d][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: 96.0%

5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-L-lyxitol (1006032-29-6) → (3aS,4R,6aR)-tetrahydro-4-([(tert-butyl)dimethylsilyloxy]methyl)-2,2-dimethylselenopheno[3,4-d][1,3]dioxole (1006032-30-9)

Guidance literature:

With selenium; sodium tetrahydroborate; In tetrahydrofuran; at 60 ℃;

DOI:10.1021/ol7025558

Reference yield: 88.0%

((3aR,6R,6aS)-Tetrahydro-2,2-dimethylselenopheno[3,4-d][1,3]dioxol-6-yl)methanol + tert-butylchlorodiphenylsilane (58479-61-1) → (3aS,4R,6aR)-tetrahydro-4-([(tert-butyl)dimethylsilyloxy]methyl)-2,2-dimethylselenopheno[3,4-d][1,3]dioxole (1006032-30-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol502899b

Reference yield:

2,3-O-isopropylidene-L-erythrofuranose (213767-09-0) → (3aS,4R,6aR)-tetrahydro-4-([(tert-butyl)dimethylsilyloxy]methyl)-2,2-dimethylselenopheno[3,4-d][1,3]dioxole (1006032-30-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 2,2,2-trifluoroethanol / toluene / 168 h / -10 °C / Inert atmosphere

1.2: 12 h / 20 °C / Inert atmosphere

2.1: hydrogen selenide; sodium tetrahydroborate / ethanol; tetrahydrofuran / 15 h / 70 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

5.1: sodium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / 1,2-dimethoxyethane / 1 h / 20 - 80 °C / Inert atmosphere

6.1: ozone / dichloromethane / 1 h / -78 °C / Inert atmosphere

6.2: 3 h / 20 °C / Inert atmosphere

7.1: sodium tetrahydroborate / tetrahydrofuran; water / 0.5 h / 20 °C / Inert atmosphere

8.1: triethylamine; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; 2,2,2-trifluoroethanol; hydrogen selenide; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; toluene; 1.1: |Wittig Olefination;

DOI:10.1021/ol502899b

upstream raw materials:

5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-L-lyxitol

tert-butylchlorodiphenylsilane

2,3-O-isopropylidene-L-lyxono-1,4-lactone

(3aR,6S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Downstream raw materials:

C₂₄H₃₂O₄SeSi

acetic acid 6-(tert-butyldiphenylsilanyloxymethyl)-2,2-dimethyltetrahydro-1,3-dioxa-5-selenapentalen-4-yl ester

7-[6-(tert-butyl-diphenylsilanyloxymethyl)-2,2-dimethyltetrahydro-1,3-dioxa-5-selenapentalen-4-yl]-6-chloro-7H-purin-2-ylamine

2-amino-6-chloro-9-(2,3-O-isopropylidene-5-O-tert-butyldiphenylsilyl-4-seleno-β-D-ribofuranosyl)-9H-purine