(2R,4S,5R)-benzyl 2-{5-[4-(tert-butyldiphenylsilanyloxy)-5-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-2-yl]thiophen-2-yl}-4-oxo-4H-chromen-3-yl carbonate

Base Information

• Chemical Name: (2R,4S,5R)-benzyl 2-{5-[4-(tert-butyldiphenylsilanyloxy)-5-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-2-yl]thiophen-2-yl}-4-oxo-4H-chromen-3-yl carbonate
• CAS No.: 1380608-61-6
• Molecular Formula: C₅₈H₅₈O₈SSi₂
• Molecular Weight: 971.331
• Mol file: 1380608-61-6.mol

Synonyms:

Chemical Property of (2R,4S,5R)-benzyl 2-{5-[4-(tert-butyldiphenylsilanyloxy)-5-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-2-yl]thiophen-2-yl}-4-oxo-4H-chromen-3-yl carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5R)-benzyl 2-{5-[4-(tert-butyldiphenylsilanyloxy)-5-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-2-yl]thiophen-2-yl}-4-oxo-4H-chromen-3-yl carbonate

There total 1 articles about (2R,4S,5R)-benzyl 2-{5-[4-(tert-butyldiphenylsilanyloxy)-5-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-2-yl]thiophen-2-yl}-4-oxo-4H-chromen-3-yl carbonate 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: 50.0%

benzyl 2-bromo-4-oxo-4H-chromen-3-yl carbonate (1332744-71-4) + C53H74O3SSi2Sn (1380608-60-5) → (2R,4S,5R)-benzyl 2-{5-[4-(tert-butyldiphenylsilanyloxy)-5-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-2-yl]thiophen-2-yl}-4-oxo-4H-chromen-3-yl carbonate (1380608-61-6)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 2h; Reflux; Inert atmosphere;

DOI:10.1021/ja3030388

Reference yield: 76.0%

(2R,4S,5R)-benzyl 2-{5-[4-(tert-butyldiphenylsilanyloxy)-5-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-2-yl]thiophen-2-yl}-4-oxo-4H-chromen-3-yl carbonate (1380608-61-6) → (2R,4S,5R)-benzyl 2-{5-[4-hydroxy-5-hydroxymethyltetrahydrofuran-2-yl]thiophen-2-yl}-4-oxo-4H-chromen-3-yl carbonate (1380608-63-8)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran;

DOI:10.1021/ja3030388

Reference yield:

(2R,4S,5R)-benzyl 2-{5-[4-(tert-butyldiphenylsilanyloxy)-5-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-2-yl]thiophen-2-yl}-4-oxo-4H-chromen-3-yl carbonate (1380608-61-6) → benzyl 2-(5-{5-[bis-(4-methoxyphenyl)phenylmethoxymethyl]-4-[(2-cyanoethoxy)diisopropylaminophosphanyloxy]tetrahydrofuran-2-yl}-thiophen-2-yl)-4-oxo-4H-chromen-3-yl carbonate

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine hydrogenfluoride / tetrahydrofuran

2: pyridine / 24 h / 20 °C

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C

With pyridine; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja3030388

upstream raw materials:

benzyl 2-bromo-4-oxo-4H-chromen-3-yl carbonate

C₅₃H₇₄O₃SSi₂Sn

Downstream raw materials:

(2R,4S,5R)-benzyl 2-{5-[4-hydroxy-5-hydroxymethyltetrahydrofuran-2-yl]thiophen-2-yl}-4-oxo-4H-chromen-3-yl carbonate