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

Base Information

• Chemical Name: (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-[(1S)-(1-hydroxy)ethynyl]-5-(1-trityloxymethyl)tetrahydrofuran
• CAS No.: 220772-74-7
• Molecular Formula: C₃₉H₅₄O₅Si₂
• Molecular Weight: 659.026

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

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

There total 10 articles about (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-[(1S)-(1-hydroxy)ethynyl]-5-(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: 65.0%

ethynylmagnesium chloride (65032-27-1) + (2S,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-formyl-5-(1-trityloxymethyl)tetrahydrofuran (220772-72-5) → (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-[(1R)-(1-hydroxy)ethynyl]-5-(1-trityloxymethyl)tetrahydrofuran + (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-[(1S)-(1-hydroxy)ethynyl]-5-(1-trityloxymethyl)tetrahydrofuran (220772-74-7)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; at -70 - 20 ℃; for 18h;

DOI:10.1021/jo020211h

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-[(1S)-(1-hydroxy)ethynyl]-5-(1-trityloxymethyl)tetrahydrofuran (220772-74-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 387 mg / imidazole / dimethylformamide / 18 h / 20 °C

2.1: 71 percent / lithium aluminium hydride / diethyl ether / 1 h / 0 °C

3.1: 68 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 6 h / -10 - 0 °C

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

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

5.1: 65 percent / ZnCl₂ / CH₂Cl₂; diethyl ether; tetrahydrofuran / 18 h / -70 - 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo020211h

Reference yield:

(2R,3S,4S,5R)-3,4-dihydroxy-2,5-di-(1-pivaloyloxymethyl)tetrahydrofuran (454474-64-7) → (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-[(1S)-(1-hydroxy)ethynyl]-5-(1-trityloxymethyl)tetrahydrofuran (220772-74-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 387 mg / imidazole / dimethylformamide / 18 h / 20 °C

2.1: 71 percent / lithium aluminium hydride / diethyl ether / 1 h / 0 °C

3.1: 68 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 6 h / -10 - 0 °C

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

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

5.1: 65 percent / ZnCl₂ / CH₂Cl₂; diethyl ether; tetrahydrofuran / 18 h / -70 - 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo020211h

upstream raw materials:

ethynylmagnesium chloride

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

trityl chloride

tert-butyldimethylsilyl chloride

Downstream raw materials:

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

(2R,3R,4R,5R,6S,9S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,9,13-tris(methoxymethoxy)-1-trityloxytetracosane

(2R,3R,4R,5R,6S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,13-bis(methoxymethoxy)-1-trityloxytetracosan-9-one

(S)-4-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-4-methoxymethoxy-butan-1-ol

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