(2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2,5-bis(1-trityloxymethyl)tetrahydrofuran

Base Information

• Chemical Name: (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2,5-bis(1-trityloxymethyl)tetrahydrofuran
• CAS No.: 454474-65-8
• Molecular Formula: C₅₆H₆₈O₅Si₂
• Molecular Weight: 877.324
• Mol file: 454474-65-8.mol

Synonyms:(2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2,5-bis(1-trityloxymethyl)tetrahydrofuran

Chemical Property of (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2,5-bis(1-trityloxymethyl)tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2,5-bis(1-trityloxymethyl)tetrahydrofuran

There total 2 articles about (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2,5-bis(1-trityloxymethyl)tetrahydrofuran 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:

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,3R,4R,5R)-3,4-dihydroxy-2,5-di(trityloxymethyl)tetrahydrofuran (68774-47-0) → (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2,5-bis(1-trityloxymethyl)tetrahydrofuran (454474-65-8)

Guidance literature:

With pyridine; 1H-imidazole; at 20 ℃; for 3h;

DOI:10.1021/jo020211h

Reference yield:

trityl chloride (76-83-5) → (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2,5-bis(1-trityloxymethyl)tetrahydrofuran (454474-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 8 h / 20 °C

2: 8.11 g / pyridine; imidazole / 3 h / 20 °C

With pyridine; 1H-imidazole;

DOI:10.1021/jo020211h

Reference yield: 83.0%

(2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2,5-bis(1-trityloxymethyl)tetrahydrofuran (454474-65-8) → (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2,5-di-(hydroxymethyl)tetrahydrofuran (220772-70-3) + (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-5-(hydroxymethyl)-2-(1-trityloxymethyl)tetrahydrofuran (220772-71-4)

Guidance literature:

With diethylaluminium chloride; In hexane; at -78 - 0 ℃; for 4h;

DOI:10.1021/jo020211h

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,3R,4R,5R)-3,4-dihydroxy-2,5-di(trityloxymethyl)tetrahydrofuran

trityl chloride

Downstream raw materials:

(2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2,5-di-(hydroxymethyl)tetrahydrofuran

(2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-5-(hydroxymethyl)-2-(1-trityloxymethyl)tetrahydrofuran

(2S,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-formyl-5-(1-trityloxymethyl)tetrahydrofuran

(2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-[(1S)-(1-hydroxy)ethynyl]-5-(1-trityloxymethyl)tetrahydrofuran