2(R)-(tert-butyldimethylsilyloxymethyl)-4(R)-azidotetrahydrofuran-3(S)-ol

Base Information

• Chemical Name: 2(R)-(tert-butyldimethylsilyloxymethyl)-4(R)-azidotetrahydrofuran-3(S)-ol
• CAS No.: 259137-54-7
• Molecular Formula: C₂₁H₂₇N₃O₃Si
• Molecular Weight: 397.549

Synonyms:2(R)-(tert-butyldimethylsilyloxymethyl)-4(R)-azidotetrahydrofuran-3(S)-ol

Chemical Property of 2(R)-(tert-butyldimethylsilyloxymethyl)-4(R)-azidotetrahydrofuran-3(S)-ol

Chemical Property:

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Technology Process of 2(R)-(tert-butyldimethylsilyloxymethyl)-4(R)-azidotetrahydrofuran-3(S)-ol

There total 4 articles about 2(R)-(tert-butyldimethylsilyloxymethyl)-4(R)-azidotetrahydrofuran-3(S)-ol 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: 78.0%

2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3R,4S)-disulfite (259137-53-6) → 2(R)-(tert-butyldimethylsilyloxymethyl)-4(R)-azidotetrahydrofuran-3(S)-ol (259137-54-7)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 3h;

DOI:10.1080/07328319908044614

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 2(R)-(tert-butyldimethylsilyloxymethyl)-4(R)-azidotetrahydrofuran-3(S)-ol (259137-54-7)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 0 °C

2: 1.04 g / SOCl₂; pyridine / 20 °C

3: 78 percent / NaN₃ / dimethylformamide / 3 h / 80 °C

With pyridine; thionyl chloride; sodium azide; In N,N-dimethyl-formamide; 1: Substitution / 2: Cyclization / 3: Ring cleavage;

DOI:10.1080/07328319908044614

Reference yield:

1,4-anhydro-D-ribitol (491-19-0,3169-91-3,3169-92-4,3999-31-3,39798-06-6,39999-42-3,41935-96-0,41936-38-3,51607-76-2,51607-78-4,53448-53-6,58716-62-4,106248-68-4,106707-70-4,120442-63-9) → 2(R)-(tert-butyldimethylsilyloxymethyl)-4(R)-azidotetrahydrofuran-3(S)-ol (259137-54-7)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 0 °C

2: 1.04 g / SOCl₂; pyridine / 20 °C

3: 78 percent / NaN₃ / dimethylformamide / 3 h / 80 °C

With pyridine; thionyl chloride; sodium azide; In N,N-dimethyl-formamide; 1: Substitution / 2: Cyclization / 3: Ring cleavage;

DOI:10.1080/07328319908044614

upstream raw materials:

2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3R,4S)-disulfite

tert-butylchlorodiphenylsilane

1,4-anhydro-D-ribitol

2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol

Downstream raw materials:

2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)-4(R)-azidotetrahydrofuran

2(R)-(tert-butyldimethylsilyloxymethyl)-4(R)-aminotetrahydrofuran-3(S)-ol

4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(hydroxymethyl)tetrahydrofuran-3(S)-ol

1,4-anhydro-2-deoxy-2-<3,4-dihydro-2,4-dioxo-5-methyl-1(2H)-pyrimidinyl>-D-arabinitol

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