(2S,3S,4R)-2-<(benzoyloxy)methyl>-3-<<(TBDMS)oxy>methyl>-4-<(methylsulfonyl)oxy>tetrahydrofuran

Base Information

• Chemical Name: (2S,3S,4R)-2-<(benzoyloxy)methyl>-3-<<(TBDMS)oxy>methyl>-4-<(methylsulfonyl)oxy>tetrahydrofuran
• CAS No.: 175876-72-9
• Molecular Formula: C₂₀H₃₂O₇SSi
• Molecular Weight: 444.621

Synonyms:(2S,3S,4R)-2-<(benzoyloxy)methyl>-3-<<(TBDMS)oxy>methyl>-4-<(methylsulfonyl)oxy>tetrahydrofuran

Chemical Property of (2S,3S,4R)-2-<(benzoyloxy)methyl>-3-<<(TBDMS)oxy>methyl>-4-<(methylsulfonyl)oxy>tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-2-<(benzoyloxy)methyl>-3-<<(TBDMS)oxy>methyl>-4-<(methylsulfonyl)oxy>tetrahydrofuran

There total 10 articles about (2S,3S,4R)-2-<(benzoyloxy)methyl>-3-<<(TBDMS)oxy>methyl>-4-<(methylsulfonyl)oxy>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:

5-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-1,2-O-isopropylidene-α-D-ribofuranose (130250-07-6) → (2S,3S,4R)-2-<(benzoyloxy)methyl>-3-<<(TBDMS)oxy>methyl>-4-<(methylsulfonyl)oxy>tetrahydrofuran (175876-72-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) TMSOTf, 2.) Et₃SiH / 1.) CH₂Cl₂, RT, 0.5 h, 2.) CH₂Cl₂, RT, 18 h

2: H₂ / 10percent Pd/C / methanol / 20 h / Ambient temperature

3: DMAP / pyridine / 23 h / Ambient temperature

4: 623 mg / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

With triethylsilane; dmap; trimethylsilyl trifluoromethanesulfonate; hydrogen; triethylamine; palladium on activated charcoal; In pyridine; methanol; dichloromethane;

DOI:10.1016/0040-4020(96)00007-5

Reference yield:

3-C-deoxy-3-C-hydroxymethyl-1,2;5,6-di-O-isopropylidene-α-D-allo-furanose (69832-48-0,119100-05-9) → (2S,3S,4R)-2-<(benzoyloxy)methyl>-3-<<(TBDMS)oxy>methyl>-4-<(methylsulfonyl)oxy>tetrahydrofuran (175876-72-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaH / 1.) DMF, RT, 40 min, 2.) DMF, RT, 13 h

2: 0.8 N H₂SO₄ / methanol / 48 h / Ambient temperature

3: NaIO₄ / methanol / 2.5 h / Ambient temperature

4: NaBH₄ / methanol / 2 h / Ambient temperature

5: pyridine / 2 h / Ambient temperature

6: 1.) TMSOTf, 2.) Et₃SiH / 1.) CH₂Cl₂, RT, 0.5 h, 2.) CH₂Cl₂, RT, 18 h

7: H₂ / 10percent Pd/C / methanol / 20 h / Ambient temperature

8: DMAP / pyridine / 23 h / Ambient temperature

9: 623 mg / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; triethylsilane; dmap; sodium tetrahydroborate; sodium periodate; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In pyridine; methanol; dichloromethane;

DOI:10.1016/0040-4020(96)00007-5

Reference yield:

(3aR,5S,6R,6aR)-6-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde (149207-10-3) → (2S,3S,4R)-2-<(benzoyloxy)methyl>-3-<<(TBDMS)oxy>methyl>-4-<(methylsulfonyl)oxy>tetrahydrofuran (175876-72-9)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBH₄ / methanol / 2 h / Ambient temperature

2: pyridine / 2 h / Ambient temperature

3: 1.) TMSOTf, 2.) Et₃SiH / 1.) CH₂Cl₂, RT, 0.5 h, 2.) CH₂Cl₂, RT, 18 h

4: H₂ / 10percent Pd/C / methanol / 20 h / Ambient temperature

5: DMAP / pyridine / 23 h / Ambient temperature

6: 623 mg / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; triethylsilane; dmap; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; hydrogen; triethylamine; palladium on activated charcoal; In pyridine; methanol; dichloromethane;

DOI:10.1016/0040-4020(96)00007-5

upstream raw materials:

methanesulfonyl chloride

(3R,4S,5R)-5-<(benzoyloxy)methyl>-4-<<(TBDMS)oxy>methyl>-tetrahydrofuran-3-ol

5-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-1,2-O-isopropylidene-α-D-ribofuranose

3-C-deoxy-3-C-hydroxymethyl-1,2;5,6-di-O-isopropylidene-α-D-allo-furanose

Downstream raw materials:

Benzoic acid (2S,3R,4S)-4-(6-amino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-ylmethyl ester

N'-{9-[(3S,4R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-9H-purin-6-yl}-N,N-dimethyl-formamidine

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