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

Base Information

Chemical Name:(2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-[(1S)-(1-methoxymethyloxy)ethynyl]-5-(1-trityloxymethyl)tetrahydrofuran
CAS No.:220772-75-8
Molecular Formula:C₄₁H₅₈O₆Si₂
Molecular Weight:703.079
Hs Code.:

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

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

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

There total 11 articles about (2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-[(1S)-(1-methoxymethyloxy)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: 90.0%

: 107-30-2
chloromethyl methyl ether

: 220772-74-7
(2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-[(1S)-(1-hydroxy)ethynyl]-5-(1-trityloxymethyl)tetrahydrofuran

: 220772-75-8
(2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-[(1S)-(1-methoxymethyloxy)ethynyl]-5-(1-trityloxymethyl)tetrahydrofuran

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 24h;
DOI:10.1021/jo020211h

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 220772-75-8
(2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-[(1S)-(1-methoxymethyloxy)ethynyl]-5-(1-trityloxymethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 6 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

6.1: 90 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 24 h / 0 - 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo020211h

Reference yield:

: 454474-64-7
(2R,3S,4S,5R)-3,4-dihydroxy-2,5-di-(1-pivaloyloxymethyl)tetrahydrofuran

: 220772-75-8
(2R,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-[(1S)-(1-methoxymethyloxy)ethynyl]-5-(1-trityloxymethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 6 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

6.1: 90 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 24 h / 0 - 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo020211h