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

Base Information

• Chemical Name: 2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol
• CAS No.: 215031-98-4
• Molecular Formula: C₂₁H₂₈O₄Si
• Molecular Weight: 372.536
• Mol file: 215031-98-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol 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-butylchlorodiphenylsilane (58479-61-1) + 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)tetrahydrofuran-(3S,4S)-diol (215031-98-4)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1080/07328319908044614

Reference yield: 99.0%

methanesulfonyl chloride (124-63-0) + 2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol (215031-98-4) → Methanesulfonic acid (2R,3R,4S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methanesulfonyloxy-tetrahydro-furan-3-yl ester

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1080/07328319908044614

Reference yield:

2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol (215031-98-4) → Benzoic acid (2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (259137-72-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.04 g / SOCl₂; pyridine / 20 °C

2: 78 percent / NaN₃ / dimethylformamide / 3 h / 80 °C

3: 87 percent / imidazole / dimethylformamide / 18 h / 70 °C

4: 93 percent / H₂ / Pd/C / ethyl acetate; ethanol / 6 h / 1292.87 Torr

5: 93 percent / toluene / 2.5 h / 0 - 20 °C

6: 54 percent / aq. H₂SO₄ / dioxane / 2.5 h / 100 °C

7: 87 percent / NH₄F / methanol / 8 h / Heating

8: 69 percent / pyridine / 2 h / -15 °C

With pyridine; 1H-imidazole; ammonium fluoride; thionyl chloride; sodium azide; sulfuric acid; hydrogen; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Cyclization / 2: Ring cleavage / 3: Substitution / 4: Reduction / 5: Addition / 6: Cyclization / 7: Substitution / 8: Acylation;

DOI:10.1080/07328319908044614

upstream raw materials:

tert-butylchlorodiphenylsilane

1,4-anhydro-D-ribitol

Downstream raw materials:

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

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

tert-butyl-(2,2-dioxo-tetrahydro-2λ⁶-furo[3,4-d][1,3,2]dioxathiol-4-ylmethoxy)-diphenyl-silane

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