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

Base Information

• Chemical Name: (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2,5-di-(hydroxymethyl)tetrahydrofuran
• CAS No.: 220772-70-3
• Molecular Formula: C₁₈H₄₀O₅Si₂
• Molecular Weight: 392.684
• Mol file: 220772-70-3.mol

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

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

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

Reference yield: 68.0%

trityl chloride (76-83-5) + (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 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(98)02439-3

Reference yield:

(2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2,5-di-(hydroxymethyl)tetrahydrofuran (220772-70-3) → (2R,3S,4S,5S,6S,9S,10S,13R,14S)-2,5:10,14-dioxido-6,9,13-tris(methoxymethoxy)-1-trityloxytetracosane-3,4-diol (220772-79-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 68 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 6 h / -10 - 0 °C

2.1: oxalyl chloride / CH₂Cl₂; dimethylsulfoxide / 1 h / -70 °C

2.2: triethylamine / CH₂Cl₂; dimethylsulfoxide / -70 - 0 °C

3.1: 65 percent / ZnCl₂ / CH₂Cl₂; diethyl ether; tetrahydrofuran / 18 h / -70 - 20 °C

4.1: 90 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 24 h / 0 - 20 °C

5.1: 78 percent / n-BuLi; anhydrous cerium chloride / tetrahydrofuran; hexane / 5 h / -78 - -23 °C

6.1: hydrogen / PtO₂ / ethyl acetate / 7 h / 20 °C

7.1: 44.5 mg / n-tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 1.2 h / 20 °C

8.1: Zn(BH₄)2 / diethyl ether / -10 °C

9.1: N,N-diisopropylethylamine / CH₂Cl₂ / 18 h / 0 - 20 °C

10.1: 47.8 mg / tetrabutylammonium fluoride / tetrahydrofuran / 5.5 h / 20 °C

With n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; cerium(III) chloride; tetrapropylammonium perruthennate; zinc(II) tetrahydroborate; oxalyl dichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate;

DOI:10.1021/jo020211h

upstream raw materials:

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

Downstream raw materials:

(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

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